- Synthesis and Cytotoxic Activity of Hexahydro-1,3,5-triazine Derivatives through Ring Condensation
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As a part of a research program for pharmacologically interacting sym-triazine derivatives with hexahydrotriazine ring, novel hexahydrotriazine derivatives (1?13) were successfully synthesized. The synthesis of hexahydrotriazines was carried out from the assembly of three molecules of various amines and three molecules of formaldehyde by “1 + 1 + 1 + 1 + 1 + 1” cycloaddition. The synthesis mechanism is probably passes through imines, which trimerizes to give the hexahydrotriazine ring. All synthesized hexahydrotriazines (1–13) were screened for their cytotoxic activity by cancer cells. As a result, compound 1–9 reduced the viability of T98G cells in a concentration-dependent manner. At a concentration of 100 μM, compound 9 exhibited the greatest cytotoxicity at 94.6%. The reason is that compound 9 is C5H5N that has a resonance hybrid structure and exhibits aromaticity. It is considered to be active because it has a structure that is a raw material for pyridine derivatives as mainly medicines and pesticides.
- Bae, Song Mi,Kang, Sung Young,Song, Ju Hyun
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p. 840 - 846
(2021/03/24)
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- Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
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A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
- Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 2619 - 2624
(2021/04/05)
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- Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation
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We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.
- Cheng, Xiao,Cai, Bao-Gui,Mao, Hui,Lu, Juan,Li, Lei,Wang, Kun,Xuan, Jun
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supporting information
p. 4109 - 4114
(2021/05/26)
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- Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines
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α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.
- Liu, Lijuan,Shi, Zhichao,Zhang, Xun,Zhan, Feng,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 3487 - 3491
(2021/09/20)
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- Ultrasound-assisted synthesis of substituted triazines and their corrosion inhibition behavior on N80 steel/acid interface
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The three substituted triazines were synthesized by ultrasound irradiation method and characterized by FTIR, 13C NMR, and 1H NMR. The corrosion inhibition behavior of the synthesized inhibitors on N80 steel in 15% HCl was studied using electrochemical analyses and weight loss methods. All three inhibitors exhibited excellent corrosion inhibition performance, and the best inhibition effect was shown by TZ-3 (93.2% at 800 mg/L). EIS measurements suggest that the corrosion inhibition process is a charge transfer controlled. The PDP results indicated that all the triazines are mixed-type inhibitors. Langmuir adsorption model is the best fit among the other tested isotherms. These molecules can act as promising acidizing corrosion inhibitors for the oil gas industry. FTIR, AFM, and UV-vis studies corroborate the adsorption of inhibitor molecules over the metal surface.
- Salman, Mohammad,Ansari, Kashif R.,Haque, Jiyaul,Srivastava, Vandana,Quraishi, Mumtaz A.,Mazumder, Mohammad A. J.
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p. 2157 - 2172
(2020/03/04)
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- Iridium-catalyzed 1,5-(aryl)aminomethylation of 1,3-enynes by alkenyl-to-allyl 1,4-iridium(i) migration
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A novel multicomponent coupling reaction involving the iridium-catalyzed 1,5-difunctionalization of 1,3-enynes with arylboronic acids and triazinanes is described. A key step in this 1,5-(aryl)aminomethylation reaction is the alkenyl-to-allyl 1,4-iridium(i) migration.
- Ruscoe, Rebecca E.,Callingham, Michael,Baker, Joshua A.,Korkis, Stamatis E.,Lam, Hon Wai
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supporting information
p. 838 - 841
(2019/01/21)
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- Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis
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A site selective C-H aminomethylation at indole's C3 position has been achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. An investigation of the mechanistic insights rationalized the essence of the activation relay and the combination mode.
- Liu, Ruixing,Liu, Jiaxin,Wei, Yin,Shi, Min
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supporting information
p. 4077 - 4081
(2019/06/14)
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- Vinylethylene Carbonates as α,β-Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition
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Herein, we report a novel stepwise addition-controlled ring size method, to access tetrahydropyrimidines through an operationally simple [3 + 3] cycloaddition of vinylethylene carbonates with triazinanes. Interestingly, we could also use this method for a [3 + 3] oxidative cycloaddition, which allows the facile synthesis of polysubstituted terphenyls under mild conditions. Mechanistic studies suggest that vinylethylene carbonates could generate α,β-unsaturated aldehydes as 3-carbon synthons for cycloaddition via a combination process of Pd-catalyzed decarboxylation and β-H elimination.
- Xu, Yi,Chen, Lu,Yang, Yu-Wen,Zhang, Zhiqiang,Yang, Weibo
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supporting information
p. 6674 - 6678
(2019/09/03)
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- Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines: Via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines
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We report a facile and efficient synthesis of spiro[imidazolidine-4,3′-indolin]-2′-imines via a copper(i)-catalyzed cascade reaction of 3-diazoindolin-2-imines with 1,3,5-triazines. The reaction proceeds under very mild conditions and tolerates a variety of functional groups. The cascade process involves the formation of a copper-carbene intermediate and a formal [2 + 2 + 1] cycloaddition.
- Zhou, Yuxuan,Ma, Fanghui,Lu, Ping,Wang, Yanguang
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supporting information
p. 8849 - 8852
(2019/10/28)
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- Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange
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The O-triethylsilylated hemiaminal Et3SiOCH2NMe2 readily transfers the Me2NCH2-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH2NMe2 readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe2 and hexahydro-1,3,5-triphenyl-1,3,5-triazine.
- McMahon,Sharma,Metta-Maga?a,Pannell
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p. 1764 - 1771
(2020/01/11)
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- Facile Access to 3-Unsubstituted Tetrahydroisoquinolonic Acids via the Castagnoli-Cushman Reaction
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Hitherto undescribed 3-unsubstituted tetrahydroisoquinolonic acids (isolated as their respective methyl esters) were accessed for the first time by the uncatalyzed, thermally promoted Castagnoli-Cushman reaction (CCR) of homophthalic anhydride (HPA) and a series of 1,3,5-triazinanes. The moderate yields observed in some cases are most likely associated with a persistent impurity also formed in these reactions. The new scaffold is expected to find novel medicinal utility (compared to the traditional CCR adducts) because it lacks a substituent at the 3-position.
- Guranova, Natalia,Dar'In, Dmitry,Krasavin, Mikhail
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p. 2001 - 2008
(2018/03/06)
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- Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates
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Here, we report a palladium-catalyzed controllable cyclization of vinyl ethylene carbonates that proceeds through formal migration [2+3] and [5+2] cycloadditions, respectively, under mild conditions. The transformation described here affords a series of synthetically versatile 5,7-membered N-heterocycles which are found in natural products and pharmaceuticals with biological and medicinal properties.
- Yang, Yuwen,Yang, Weibo
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supporting information
p. 12182 - 12185
(2018/11/21)
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- Synthesis of hexahydro-symtriazines using PEG-400 as superior solvent
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1,3,5-Hexahydrotriazine derivatives show broad spectrum of biological activities such as anticancer, antitumor. Some of their derivatives are used as carcenolytics, herbicides and show antidote and growth stimulating activities. Very few methodologies are reported for the synthesis of symtriazines. Synthesis of trimer of hexahydrotriazines is pH sensitive reaction and instead of using any acidic and basic conditions, we tried to synthesize this trimer under neutral conditions. Methods: Synthesis of 1,3,5-hexahydro symtriazine derivatives has been achieved by treating parasubstituted aniline with solution of paraformaldehyde using PEG-400 as neutral medium using grindstone method. Results: Symtriazine derivatives were synthesized in good to excellent yields (95-70%) within a short time of 5-7 minutes by grindstone technique using PEG-400 as neutral solvent medium. All the synthesized compounds were characterized by 1HNMR, 13CNMR, Mass and Melting point. Conclusion: This is the first report for the synthesis of 1,3,5-hexahydro-sym-triazine trimer starting from aniline/substituted aniline and paraformaldehyde in the presence of reusable and environmental friendly solvent media PEG-400 by grindstone technique.
- Bondle, Giribala M.,Jadhav, Rohit G.,Kamble, Vinod T.,Atkore, Sandeep T.
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- Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights
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A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.
- Zheng, Yang,Chi, Yongjian,Bao, Ming,Qiu, Lihua,Xu, Xinfang
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p. 2129 - 2135
(2017/02/26)
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- Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes
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Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.
- Gong, Jun,Li, Shi-Wu,Qurban, Saira,Kang, Qiang
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supporting information
p. 3584 - 3593
(2017/07/22)
-
- Synthesis of an intrinsically flame retardant bio-based benzoxazine resin
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An intrinsically flame retardant bio-based benzoxazine (diphenolic acid pentaerythritol caged phosphate benzoxazine, DPA-PEPA-Boz) monomer was synthesized from bio-based diphenolic acid (DPA) using a four-step process. The monomer of DPA-PEPA-Boz was characterized by FT-IR, 1H NMR and 13C NMR. The curing behavior of DPA-PEPA-boz was studied and compared with those of DPA based benzoxazine (DPA-Boz) and DPA ester derivative (MDP) based benzoxazine (MDP-Boz) without PEPA by means of non-isothermal differential scanning calorimetry. The results indicated that DPA-PEPA-Boz system showed a two-stage curing, assigned to the exothermic opening reactions of oxazine rings and P-O-C ring in PEPA respectively, while the DPA-Boz and MDP-Boz showed a one-stage curing. In addition, the effect of the introduction of PEPA on thermal and inflammable properties of the resin was evaluated. The residual char of the cured DPA-PEPA-Boz (P-DPA-PEPA-Boz) after 400 °C was much higher than those of cured DPA-Boz (P-DPA-Boz) and cured MDP-Boz (P-MDP-Boz) under nitrogen and air atmospheres. Meanwhile, total heat release (THR), peak heat release rate (PHRR) and heat release capacity (HRC) of P-DPA-PEPA-Boz were about half of those of P-DPA-Boz and P-MDP-Boz. P-DPA-PEPA-Boz had a limiting oxygen index (LOI) of 33.5% and achieved V0 rating in UL94 test. P-DPA-PEPA-Boz behaved as a very good intrinsic thermal and flame retardant bio-based benoxazine resin.
- Yan, Hongqiang,Sun, Chuang,Fang, Zhengping,Liu, Xiaoqing,Zhu, Jin,Wang, Hao
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p. 418 - 427
(2016/06/09)
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- Gold-Catalyzed Formal [4+1]/[4+3] Cycloadditions of Diazo Esters with Triazines
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Reported herein is the unprecedented gold-catalyzed formal [4+1]/[4+3] cycloadditions of diazo esters with hexahydro-1,3,4-triazines, thus providing five- and seven-membered heterocycles in moderate to high yields under mild reaction conditions. These reactions feature the use of a gold complex to accomplish the diverse annulations and the first example of the involvement of a gold metallo-enolcarbene in a cycloaddition. It is also the first utilization of stable triazines as formal dipolar adducts in the carbene-involved cycloadditions. Mechanistic investigations reveal that the triazines reacted directly, rather than as formaldimine precursors, in the reaction process.
- Zhu, Chenghao,Xu, Guangyang,Sun, Jiangtao
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supporting information
p. 11867 - 11871
(2016/11/17)
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- Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That can be Trapped as Their [Mo(CO)4] Complexes
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Compound Et3SiOCH2NMe2 transfers Me2NCH2 to R2NH (R2=Et2, PhMe, [Cr(η6-C6H5)(CO)3]Me, PhH) to form previously unknown diaminomethanes, Me2NCH2NR2 and, in the case of R2=PhH, the triamine Me2NCH2N(Ph)CH2NMe2. The diaminomethanes exhibit an unreported disproportionation to a mixture of (R2N)2CH2, (Me2N)2CH2, and Me2NCH2NR2, which can be trapped as their [Mo(CO)4(diamine)] complexes. Whereas PhMeNCH2NMe2 is a labile material, the metal-substituted ([(η6-C6H5)Cr(CO)3]MeNCH2NMe2 is a stable material. The triamine Me2NCH2N(Ph)CH2NMe2 is unstable with respect to transformation to 1,3,5-triphenyltriazine, but is readily trapped as the bidentate-triamineMo(CO)4. All metal complexes were characterized by single-crystal X-ray diffraction.
- Sharma, Hemant K.,Gonzalez, Paulina E.,Craig, Alexander L.,Chakrabarty, Sanchita,Metta-Maga?a, Alejandro,Pannell, Keith H.
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p. 7363 - 7366
(2016/05/24)
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- Study on products and reaction paths for synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine from phenol, aniline and formaldehyde
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To study the synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine (benzoxazine), the reaction paths of phenol, aniline and formaldehyde were investigated by analyzing the synthesis crude products. With the aid of high-performance liquid chromatography (HP
- Zhang, Cheng-Xi,Deng, Yu-Yuan,Zhang, Yi-Yang,Yang, Po,Gu, Yi
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p. 348 - 352
(2015/04/14)
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- Task-specific ionic liquid-mediated facile synthesis of 1,3,5 triaryltriazines by cyclotrimerization of imines and their biological evaluation
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A highly efficient method for the synthesis of fluorinated 1,3,5-triaryltriazine derivatives is developed by the condensation reaction of aromatic amines and formaldehyde followed by spontaneous cyclotrimerization using task-specific 1,1,3,3-tetramethylguanidine trifluoroacetate [TMG][Tfa] ionic liquid as a environmentally benign solvent in excellent yields at room temperature. The synthesized compounds were subjected for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain using the LoewensteinJensen medium.
- Dandia, Anshu,Jain, Anuj K.,Sharma, Sonam
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supporting information
p. 521 - 523
(2014/04/17)
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- A facile and efficient ultrasound-assisted synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazine through mannich reaction
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In this paper, we report a facile and efficient method for the synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazines by reaction of formaldehyde and aromatic amines catalyzed by triethylamine (Et3N) and assisted by ultrasound at rt. This method has the advantages of short reaction times, good.
- Zhong, Xiaoxing,Dou, Guolan
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p. 877 - 883
(2013/05/08)
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- Synthesis of N-substituted 1,3,5-triazacyclohexanes catalyzed by starch sulfuric acid
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N-substituted 1,3,5-triazacyclohexanes were simply synthesized from the reaction of aromatic or fatty amines and formaldehyde catalyzed by recyclable starch sulfuric acid with good yields at room temperature.
- Wu, Hui,Yuan, Rui,Wan, Yu,Yin, Wei,Pang, Li-Ling
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experimental part
p. 1097 - 1102
(2012/03/11)
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- Novel oxidative nitrogen to carbon rearrangement found in the conversion of anilines to benzaldoximes by treating with HCHO/H2O2
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Novel rearrangement was found by reacting anilines with HCHO/H2O2 resulting in the synthesis of various benzaldoximes. The mechanism of the rearrangement is proposed and suggested that the rearrangement might proceed via unstable N-phenyloxazirane intermediate followed by the transfer of aryl moiety from nitrogen to carbon atom leading to the formation of benzaldoxime.
- Kapuriya, Naval,Kapuriya, Kalpana,Dodia, Narsinh M.,Lin, Yi-Wen,Kakadiya, Rajesh,Wu, Chao-Ting,Chen, Ching-Huang,Naliapara, Yogesh,Su, Tsann-Long
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p. 2886 - 2890
(2008/09/21)
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- Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines
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Enantiopure (1R,2S)-1-benzyl- and 1-arylaziridine-2-carboxamides were obtained by kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis. Several regio- and enantioselective nucleophilic ring openings of (1R,2S)-1-benzylaziridine-2-carboxamide or its LAH-reduced product led to a series of enantiopure products, such as O-methyl-L-serine and some vicinal diamines.
- Moran-Ramallal, Roberto,Liz, Ramon,Gotor, Vicente
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p. 521 - 524
(2007/10/03)
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- Synthesis and oxidative ring contraction of 1,5,3,7-dichalcogenadiazocanes. Novel formation of 1,2,4-diselenazolidines, 1,2,4-ditellurazolidines, and 1,2,3,4,5,7-pentathiazocanes
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1,5,3,7-Dithiadiazocanes, 1,5,3,7-diselenadiazocanes, and 1,5,3,7-ditelluradiazocanes were prepared from a primary amine, formalin, and H2S, NaSeH, or NaTeH, respectively. Oxidation of 1,5,3,7- diselenadiazocanes and 1,5,3,7-ditelluradiazocanes using NBS efficiently afforded 1,2,4-diselenazolidines or 1,2,4-ditellurazolidines, respectively. In contrast, treatment of 1,5,3,7-dithiadiazocanes with bromine-elemental sulfur or disulfur dichloride (S2Cl2) afforded 1,2,3,4,5,7- pentathiazocanes. An unusual oxidative conversion of 1,5,3,7- dichalcogenadiazocanes into these products was assumed to proceed through in situ formation of 1,5,3,7-dichalcogenadiazabicyclo[3.3.0]octane-type dications.
- Takikawa, Yuji,Koyama, Yutaka,Yoshida, Takamasa,Makino, Kenshiro,Shibuya, Hiroki,Sato, Kazuto,Otsuka, Tatsuya,Shibata, Yuko,Onuma, Yuki,Aoyagi, Shigenobu,Shimada, Kazuaki,Kabuto, Chizuko
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p. 1913 - 1925
(2007/10/03)
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- CYCLIC COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PEST CONTROL AGENT
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A compound represented by the formula: wherein, A represents a group represented by the formula: CY1Y2OCY3Y4, CY1Y2SOnCY3Y4, CY1Y2NRCY3Y4, CY1=NCY3Y4 or CY1Y2N=CY3 (wherein n is 0, 1, or 2, and Y1, Y2, Y3, and Y4 each independently represents hydrogen, alkyl, or haloalkyl); R represents hydrogen, halogen, an optionally substituted hydrocarbon group, etc.; Q1 represents substituted phenyl or a substituted aromatic heterocyclic group; and Q2 represents substituted phenyl, alkyl, or haloalkyl, or a salt. thereof; a process for producing the. compound or a salt thereof; and an insecticide containing. the same. Besides being applicable by spraying, the insecticide can be used for soil treatment and seed treatment.
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- An efficient approach to 1,3,5-tris-arylhexahydro-1,3,5-triazines
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In this paper we report a facile and efficient procedure for the synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazines (3) by reaction of anilines 1 with 1,3,6,8-tetrazatricyclo[4.4.1.13,8]-dodecane (TATD) (2). The diequatorial chair conformational preference of 3b (Ar=p-tolyl) in the solid state was established by X-ray crystallography and agrees well with molecular mechanics calculations.
- Rivera, Augusto,Torres, Olga Lucia,Leiton, Jesus D.,Morales-Rios, Martha S.,Joseph-Nathan, Pedro
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p. 1407 - 1414
(2007/10/03)
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- Synthesis of 1,2,4-ditellurazolidines by oxidative ring contraction of 2H,6H-tetrahydro-1,5,3,7-ditelluradiazocines
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Synthesis of novel five-membered cyclic ditellurides, 4-aryl-1,2,4-ditellurazolidines was achieved by treating 3,7-diaryl-2H,6H-tetrahydro-1,5,3,7-ditelluradiazocines with oxidizing agents or by aerobic exposure. The oxidative ring contraction of the heterocycles was assumed to proceed through formation and subsequent fragmentation of bicyclic ditellura dications.
- Takikawa, Yuji,Yoshida, Takamasa,Koyama, Yutaka,Sato, Kazuto,Shibata, Yuko,Aoyagi, Shigenobu,Shimada, Kazuaki,Kabuto, Chizuko
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p. 870 - 871
(2007/10/03)
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- A comparison of some pyrolysis reactions of benzotriazoles, benzisoxazolones and benzisothiazolones
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The products of flash vacuum pyrolysis of N-acetyl, N-methyl, N-benzyl and N-heteroaryl-substituted benzotriazole, 2,1-benzoxazol-3-one and 2,1-benzothiazol-3-one have been compared. The pyrolysis of benzotriazoles and benzisoxazolones appears to involve an iminocarbene intermediate, although the N-benzyl analogues react by radical pathways. Benzisothiazolones appear to form iminoketene intermediates.
- Janowski, Wit K.,Prager, Rolf H.,Smith, Jason A.
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p. 3212 - 3216
(2007/10/03)
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- Flash Vacuum Thermolysis of Four Membered Rings Containing Nitrogen Atom. Part IV. Some Mechanistic Aspects of the Thermal Decomposition of Azetidines
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Thermal cycloreversions of substituted azetidine rings under FVT conditions have been studied.It was found that the regiochemistry of these reactions depends on the nature of substituents present in the system.The assumed 1,4-diradical stepwise mechanism enabled us to compare the competition in breaking of the first bond (N-C2 or C2-C3) depending on the stability of newly formed 1,4-diradical. - Keywords: azetidines, flash vacuum thermolysis
- Lesniak, S.
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p. 1484 - 1489
(2007/10/03)
-
- DESILYLATION OF α-TRIMETHYLSILYL NITRAMINES : THE FIRST NITRAMINE α-ANION
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Fluoride induced desilylation of a trimethylsilylcyclopropyl nitramine generated the first known nitramine α-anion, which was trapped in situ by electrophiles (H2O, D2O and CH3CHO).In contrast, a trimethylsilylmethyl nitramine gave a product resulting from elimination of the elements of trimethylsilyl nitrite under identical reaction conditions.
- Lillya, C. Peter,Sassi, Thomas P.
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p. 6133 - 6134
(2007/10/02)
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- Preparation of N,O-Aminals as Synthetic Equivalents of H2C=NAr and (H2C=NHAr)+ ions: Neutral- and Acid-promoted Transformations
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A general method for the synthesis of N, O-aminals derived from primary aromatic amines is described.The reactivity of these compounds under neutral and acidic conditions has been studied and the title compounds can be envisaged as general purpose H2C=NAr or (H2C=NAr)+ equivalents.N,O-Aminals have been converted into perhydrotriazines by moderate heating and into bis(4-aminoaryl)methane derivatives or N-benzylarylamines, respectively, when heated in acidid media with pH control.Reduction od N,O-acetals with sodium cyanoborohydride has revealed that the C-O bond is broken exclusively in acidic media.
- Barluenga, Jose,Bayon, Ana M.,Campos, Pedro,Asensio, Gregorio,Gonzalez-Nunez, Elena,Molina, Yolanda
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p. 1631 - 1636
(2007/10/02)
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- Revisitation of Formaldehyde-Aniline Condensation. III. The Cyclic Tetramer of N-Methyleneaniline: An X-Ray Diffraction Structure Determination
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The cyclic tetramer of N-methyleneaniline, one of the products from the condensation between formaldehyde and aniline under neutral condition, has been characterized as 1,3,5,7-tetraphenyltetrazocine (3) and its crystal structure elucidated by X-ray diffraction.
- Randaccio, Lucio,Zangrando, Ennio,Gei, Maria H.,Giumanini, Angelo G.
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p. 187 - 194
(2007/10/02)
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- Revisitation of Formaldehyde Aniline Condensation. VII. 1,3,5-Triarylhexahydro-sym-triazines and 1,3,5,7-Tetraaryl-1,3,5,7-tetrazocines from Aromatic Amines and Paraformaldehyde
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A product study of the reaction between a number of aromatic amines substituted with widely different groups and paraformaldehyde in inert solvents was performed and found to yield 1,3,5-triaryl-1,3,5-hexahydrotriazines, 1,3,5,7-tetraaryl-1,3,5,7-tetrazocines and formaminals.It was not possible to correlate the product outcomes with the actual structure of the amine substrate.The X-ray diffraction structural determination of 1,3,5-tri-(t-butylphenyl)- (1b) and 1,3,5-tri-(m-fluorophenyl)-1,3,5-hexahydrotriazine (1c) showed the diaxial arrangement of the N-substituents.
- Giumanini, Angelo G.,Verardo, Giancarlo,Zangrando, Ennio,Lassiani, Lucia
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p. 1087 - 1103
(2007/10/02)
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- Revisitation of Formaldehyde Aniline Condensation. I. High Yield Synthesis of 1,3,5-Triphenylhexahydro-sym-triazine and its X-Ray Crystal Structure Determination
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A rapid and efficient preparation of 1,3,5-triphenylhexahydro-sym-triazine (10) using paraformaldehyde is reported.The trimeric nature of the compound and its structure in solid state, where a biaxial chair conformation is favoured, are conclusively shown by X-ray diffraction analysis.A recent report on a preparation of 1,3-diphenyl-1,3-diazetidine is invalidated.
- Giumanini, Angelo G.,Verardo, Giancarlo,Randaccio, Lucio,Bresciani-Pahor, Nevenka,Traldi, Pietro
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p. 739 - 748
(2007/10/02)
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- THE RESISTANCE TO HYDROLYSIS OF N,N-DIMETHYL-N-PHENYLAMMONIOMETHANESULFONATE AND THE IMPROBABILITY OF A RECENTLY-PROPOSED MECHANISM OF HYDROLYSIS OF ANILINOMETHANESULFONATES.
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The hydrolysis of PhN(1+)Me2CH2SO3(1-) (2) is so slow that a proposed mechanism of hydrolysis of PhNHCH2SO3(1-) Na(1+) involving SN2 attack of H2O on PhNH2(1+)CH2SO3(1-) may be discounted.
- King, J. F.,Skonieczny, S.
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p. 2533 - 2534
(2007/10/02)
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- The Pyrolysis of N-Allyl Compounds: Free-radical and Retro-ene Mechanisms
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Flash vacuum pyrolysis of N-alkyl-N-allylanilines gives imines by free radical cleavage of the allyl group followed by loss of an atom (or group of atoms) from the α-carbon atom of the alkyl group.The corresponding N-propargyl derivatives also give imines on pyrolysis, but the mechanism is a concerted retro-ene process which may lead to different products from the corresponding N-allyl compound.N-Allyl-N,N-dialkylamines also decompose thermally by a retro-ene process
- Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
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p. 2247 - 2273
(2007/10/02)
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- Photochemistry of N-nitroso-N-alkyl amino acids: a facile oxidative decarboxylation
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Several N-alkyl or N-phenyl-N-nitroso α-amino acids were synthesized and were shown to photolytically rearrange to amidoximes with concurrent decarboxylation in solution or solid states without the presence of externally added acids.In contrast, N-nitrosonipecotinic acid, a N-nitroso β-amino acid, as well as N-nitrosopiperidine in the presence of acetic acid were not photolabile.The photolability of N-nitroso α-amino acids was ascribed to the presence of an intramolecular association between the nitrosamino and carboxyl groups through hydrogen bonding.The species having the hydrogen bonding through the nitroso oxygen in the Z-configuration was believed to be photolabile and decomposed to alkylideneimines as the primary product.The mechanism of the oxidative photorearrangement was discussed.
- Chow, Yuan L.,Horning, Douglas P.,Polo, Joel
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p. 2477 - 2483
(2007/10/02)
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- Light-induced Reactions of 2-(N-Alkyl-N-arylamino)acetophenones and Related Amino-ketones: Formation of 1,3-Diarylazetidin-3-ols
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On irradiation in ether, 2-(N-methylanilino)acetophenones, Ar1NMe-CH2COAr2 (Ar1,Ar2=Ph,Ph; Ph,p-MeO-C6H4; Ph,p-Ph-C6H4; p-Cl-C6H4,Ph; p-MeO-C6H4,Ph; and p-Me-C6H4,Ph), underwent type II cyclisation to isomeric 1,3-diarylazetidin-3-ols.A minor photoproduct was one of the two expected type II fission products, the corresponding acetophenone Ar2COMe.The second type II fission product, imine Ar1N=CH2, was not detected, but in three cases a 1,3-diarylimidazolidine, probably derived from this imine, was isolated.Similar results were obtained on irradiation of the related amino-ketones, 2-(N-methylanilino)-2'-acetonaphthone and 2-(N-methylanilino)-1-tetralone.Direct fission of the C-2-N bond occured on irradiation of 2-(N-methylanilino)indan-1-one and 2,2-dimethyl-2-(N-methylanilino)acetophenone. 2-(N-Alkylanilino)acetophenones, PhNR-CH2COPh (R=Et, Me2CH, and PHCH2), yielded complex mixtures on irradiation.
- Allworth, Keith L.,EI-Hamamy, Ahmad A.,Hesabi, Massoud M.,Hill, John
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p. 1671 - 1678
(2007/10/02)
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- Tetrahydro-1,3,5-thiadiazin-4-one derivative
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A tetrahydro-1,3,5-thiadiazin-4-one represented by the general formula, STR1 wherein R1, R2 and R3, which may be the same or different, represent each an alkyl group, allyl group, cycloalkyl group, alkoxyalkyl group, benzyl group, phenyl group or substituted phenyl group having as substituents alkyl groups, nitro group, halogen atoms, alkoxy groups, or trifluoromethyl group and R2 and R3 may also represent hydrogen atoms, is a new compound and useful for controlling insects and mites.
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