- Synthetic approaches to Cinchona alkaloids: The C-8/C-9 disconnection strategy
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When conducted in DMSO, the Hünig's base-promoted condensation of 3-quinuclidinone with quinoline-4-carboxaldehyde gave an equimolar mixture of epimeric aldols 8 with an excellent yield.
- Jankowski, Rapha?l,Joseph, Delphine,Cavé, Christian,Dumas, Fran?oise,Ourevitch, Michèle,Mahuteau, Jacqueline,Morgant, Georges,Pavlovi?, Nada Bosnjakovi?,D'Angelo, Jean
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- Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes
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A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.
- Xu, Jincheng,Li, Yang,Ding, Tianling,Guo, Hao
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supporting information
p. 3114 - 3117
(2021/09/03)
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- Hydroxymethylation of quinolinesviairon promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives
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Herein, we report a mild and efficient hydroxymethylation of quinolinesviaan iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.
- Shantharjun, Bangarigalla,Vani, Damera,Unnava, Ramanjaneyulu,Sandeep, Mummadi,Reddy, Kallu Rajender
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p. 645 - 652
(2021/02/06)
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- Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity
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Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.
- Mao, Kaining,Nutting, Jordan E.,Stahl, Shannon S.
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supporting information
p. 10565 - 10570
(2021/07/28)
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- Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System
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An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.
- Hu, Qi-Qi,Gao, Yan-Ting,Sun, Jia-Chen,Gao, Jing-Jing,Mu, Hong-Xiao,Li, Yi-Ming,Zheng, Ya-Nan,Yang, Kai-Rui,Zhu, Yan-Ping
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supporting information
p. 9000 - 9005
(2021/11/24)
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- Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides
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An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.
- Shang, Zhi-Hao,Sun, Ji-Na,Guo, Jiang-Shan,Sun, Yuan-Yuan,Weng, Wei-Zhao,Zhang, Zhen-Xiao,Li, Zeng-Jing,Zhu, Yan-Ping
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supporting information
(2020/01/08)
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- Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds
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A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.
- Gao, Xianying,Han, Shuaijun,Zheng, Maolin,Liang, Apeng,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie,Li, Jingya
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supporting information
p. 4040 - 4049
(2019/04/30)
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- Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes
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A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.
- Ye, Rongzi,Cao, Yuanjie,Xi, Xiaoxiang,Liu, Long,Chen, Tieqiao
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supporting information
p. 4220 - 4224
(2019/05/10)
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- Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent
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A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.
- Huang, He,Li, Xiangmin,Yu, Chenguang,Zhang, Yueteng,Mariano, Patrick S.,Wang, Wei
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supporting information
p. 1500 - 1505
(2017/02/05)
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- Copper-Catalyzed Aerobic Oxidation of Azinylmethanes for Access to Trifluoromethylazinylols
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A copper-catalyzed oxygenation of methylazaarenes was found to occur in the absence of both ligand and additive, and has been successfully employed for the synthesis of trifluoromethylazinylketols. This synthetic strategy incorporates aerobic oxidation and a trifluoromethylation in one-pot and provides a novel method for the trifluoromethylation of aliphatic C-H bond.
- Zheng, Gang,Liu, Hao,Wang, Mang
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supporting information
p. 519 - 523
(2016/06/01)
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- Catalytic Aerobic Photo-oxidation of a Methyl Group on a Heterocycle to Produce an Aldehyde via Homolytic C-I Bond Cleavage caused by Irradiation with Visible Light
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A new catalytic method was developed for photo-oxidizing the methyl group on aromatic heterocycles such as benzothiazole, benzoxazole, and quinoline to produce the corresponding aldehyde. This is the first report of the metal-free catalytic synthesis of benzothiazole-2-carboxaldehydes using molecular oxygen as the terminal oxidant.
- Nagasawa,Tachikawa,Yamaguchi,Tada,Miura,Itoh
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supporting information
p. 178 - 182
(2016/02/14)
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- Selective photosensitization through an and logic response: Optimization of the pH and glutathione response of activatable photosensitizers
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A series of pH and GSH responsive photosensitizers were designed and synthesized. pKa values were optimized by adjusting the inductive contribution of substituents to reach a pH range (6.0-7.4) relevant to the tumour microenvironment. pH-Activatable behaviour and redox mediated release of the quencher from the PS by GSH allow the construction of an AND logic operator for selective photodynamic action in aqueous solutions.
- Erbas-Cakmak, Sundus,Cakmak, Fatma Pir,Topel, Seda Demirel,Uyar, Taha Bilal,Akkaya, Engin U.
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supporting information
p. 12258 - 12261
(2015/07/27)
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- An expedient osmium(vi)/K3Fe(CN)6-mediated selective oxidation of benzylic, allylic and propargylic alcohols
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A chemoselective osmium(vi) catalyzed oxidation of benzylic, allylic and propargylic alcohols using K3Fe(CN)6as a secondary oxidant is described. This protocol is operationally simple and exhibits excellent chemoselectivity favouring the oxidation of benzylic alcohols over the aliphatic alcohols. A larger scale reaction was also found to be compatible. This journal is
- Fernandes, Rodney A.,Bethi, Venkati
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p. 40561 - 40568
(2015/02/18)
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- Synthesis and anti-norovirus activity of pyranobenzopyrone compounds
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During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 μM and TD50 values of >200 and 96.4 μM, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents.
- Pokhrel, Laxman,Kim, Yunjeong,Nguyen, Thi D.T.,Prior, Allan M.,Lu, Jianyu,Chang, Kyeong-Ok,Hua, Duy H.
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supporting information; experimental part
p. 3480 - 3484
(2012/07/03)
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- Identification of trans-4-[1-[[7-fluoro-2-(1-methyl-3-indolyl)-6- benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid as a potent, orally active VLA-4 antagonist
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For the purpose of obtaining orally potent VLA-4 inhibitors, we have carried out structural modification of the (N′-phenylureido)phenyl group in compound 1, where the group was found to be attributed to poor pharmacokinetic profile in our previous research. Through modification, we have identified several compounds with both potent in vitro activity and improved oral exposure. In particular, compound 7e with 7-fluoro-2-(1-methyl-1H-indol-3- yl)-1,3-benzoxazolyl group as a novel replacement of the (N′-phenylureido) phenyl group significantly inhibited eosinophil infiltration into bronchoalveolar lavage fluid at 15 mg/kg in an Ascaris-antigen-induced murine bronchial inflammatory model, and its efficacy was comparable to that of the anti-mouse α4 antibody (R1-2).
- Setoguchi, Masaki,Iimura, Shin,Sugimoto, Yuuichi,Yoneda, Yoshiyuki,Chiba, Jun,Watanabe, Toshiyuki,Muro, Fumihito,Iigo, Yutaka,Takayama, Gensuke,Yokoyama, Mika,Taira, Tomoe,Aonuma, Misato,Takashi, Tohru,Nakayama, Atsushi,MacHinaga, Nobuo
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scheme or table
p. 1201 - 1212
(2012/03/26)
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- Synthesis of conjugated (1E,3E)- and (1Z,3Z)-1,4-di(n-pyridyl) (or n-quinolyl)-1,3-butadienes from n-(2′-chloroethenyl)pyridine (or quinoline)
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The homocoupling reaction between the conjugated n-(2-chloroethenyl)pyridine; n, 2-, 3- and 4- (or quinoline; n, 2- and 4-) mediated by zero-valent nickel complexes at room temperature affords to the corresponding 1,4-diaryl-1,3-butadiene, always as the 1E,3E stereoisomer. The yield in 1,4-diaryl-1,3-butadiene increases with the nickel catalyst and hence, the active zero-valent nickel catalyst is not regenerated during the homocoupling reaction. The stereospecific synthesis of (1Z,3Z)-1,4-di(4′-pyridyl)-1,3-butadiene stereoisomer was efficiently carried out by partial hydrogenation of the appropriate 1,4-di(4′-pyridyl)-1,3-butadiyne.
- Rodríguez,Díaz-Oliva, Cristina
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experimental part
p. 2512 - 2517
(2009/08/07)
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- Alkaloids from Nitraria komarovii. Structures of nitraridine, dihydronitraridine, and tetrahydronitraridine
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Three new alkaloids nitraridine (1), dihydronitraridine (2), and tetrahydronitraridine (3) were isolated from the aerial part of Nitraria komarovii. Their structures were established based on chemical transformations and spectral data. The compounds were synthesized. Spectral properties of the komarovine subgroup of alkaloids were discussed.
- Tulyaganov
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p. 459 - 461
(2008/02/09)
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- A new family of quinoline and quinoxaline analogues of combretastatins
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The 3-hydroxy-4-methoxyphenyl ring of combretastatin A-4 can be replaced by a 2-naphthyl moiety without significant loss of cytotoxicity and inhibition of tubulin polymerization potency. In this paper we show that the 6- or 7-quinolyl systems can in turn replace both cyclic moieties, keeping in the first case most of the potency as cytotoxic agent and in the second case as inhibitor of tubulin polymerization, related to the activities displayed by model compounds.
- Perez-Melero, Concepcion,Maya, Ana B.S.,Del Rey, Benedicto,Pelaez, Rafael,Caballero, Esther,Medarde, Manuel
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p. 3771 - 3774
(2007/10/03)
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- Improved oxidation of active methyl group of N-heteroaromatic compounds by selenium dioxide in the presence of tert-butyl hydroperoxide
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The oxidation of active methyl group of N-heteroaromatic compounds including both of bicyclic and monocyclic compounds using SeO2 was considerably improved in the presence of tert-butyl hydroperoxde in dioxane to give the corresponding aldehyde or carboxylic acid in the moderate to good yields. The present oxidation proceeds more mildly and more selectively to form aldehyde rather than carboxylic acid, compared with conventional SeO2 oxidation without tert-butyl hydroperoxide.
- Tagawa, Yoshinobu,Yamashita, Katsuya,Higuchi, Yoshitaka,Goto, Yoshinobu
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p. 953 - 957
(2007/10/03)
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- Inhibitors of glycogen synthase kinase 3
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Novel pyridine and pyrimidine derivatives which selectively inhibit glycogen synthase kinase 3 are provided and methods of preparing these compounds are provided. These compounds are useful in treating certain conditions which may be mediated by glycogen synthase kinase 3.
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- A new approach to the oxidation of methylquinolines with selenium dioxide
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A study of some parameters which influence the oxidation of 2- and 4-methylquinolines with selenium dioxide (or selenious acid) in dioxane has allowed to correct some erroneous opinions of this method and to elaborate a general, simple, fast, and cheap procedure of oxidation of methylquinolines having a methyl group in the position 2 or 4.
- Achremowicz, Lucjan
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p. 1681 - 1684
(2007/10/03)
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- SYNTHESIS AND CONFIGURATION OF SOME NEW BICYCLIC 3-ARYLIDENE- AND 3-HETEROARYLIDENE-2-OXINDOLES
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The synthesis of a novel class of bicyclic 3-arylidene- and 3-heteroarylidene-2-oxindoles possessing tyrosine kinase inhibitory activity is described.Compounds 1-16 have been prepared by condensation of 2-oxindole with a (hetero)aromatic aldehyde belonging to the naphthalene, tetralin, quinoline or indole series.The compounds so obtained were single E or Z isomers or separable mixtures thereof.The single E or Z isomers could be partially transformed into their isomers by acid or basic catalysis.The E/Z configuration assignment was achieved by 1H NMR spectroscopy on the basis of chemical shifts and NOE data obtained from NOESY spectra.
- Buzzetti, Franco,Pinciroli, Vittorio,Brasca, M. Gabriella,Crugnola, Angelo,Fustinoni, Silvia,Longo, Antonio
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- Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.
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To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.
- Hashizume,Ito,Yamada,Nagashima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
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p. 512 - 520
(2007/10/02)
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- Synthesis of a Simple Model Compound of Dynemicin and Cycloaromatization with Pinacol-Pinacolone Rearrangement in the Strained Enediyne Medium Ring
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Novel bicyclo-tridecdiyne system included in dynemicin was synthesized from a quinoline aldehyde in 9 steps.Key step was the cyclization with silyl acetylene to ketone carbonyl group through fluoride activation with CsF.The cyclized compound did aromatize under acidic condition, with opening of the epoxide ring, to give a Bergman product that was further converted with pinacol-pinacolone rearrangement.
- Nishikawa, Toshio,Ino, Akira,Isobe, Minoru,Goto, Toshio
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p. 1271 - 1274
(2007/10/02)
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- Synthesis of 4-Vinylquinoline: Pyrolytic Rearrangement of the 4-(1-Hydroxyethyl)quinoline and Related Derivatives
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The synthesis of 4-vinylquinoline has been carried out by means of the Wittig reaction between 4-quinolinecarbaldehyde and the methyl triphenylphosphonium ylide in dimethyl sulphoxide in good yield.Dehydration of the 4-(1-hydroxyethyl)quinoline and their xanthate derivative, give equimolar amounts of 4-ethylquinoline and 4-acetylquinoline while small amounts of 4-vinylquinoline were found.Dehydrochlorination of 4-(1-chloroethyl)quinoline in ethanol-sodium hydroxide provides 4-ethyl-3-ethoxyquinoline in good yield, but 4-vinylquinoline is a minor reaction product.
- Rodriguez, J. G.,Benito, Y.
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p. 819 - 821
(2007/10/02)
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- Synthesis of Oxaziridinylquinones and Oxaziridinylazines as Potential Antitumor Agents
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1,4-Benzoquinones, 1,4-naphthoquinones, as well as pyridines and quinolines having 2-alkyloxaziridinyl substituents were synthesized.The method involves formation of aldimines and their oxidation to oxaziridines. 1,4-Dimethoxyarenes bearing oxaziridinyl substituents were converted into the corresponding quinones with silver(II) dipicolinate.Some of the oxaziridinylquinones and -azines exhibit activity against KB cells, and the structure-activity relationship is discussed in terms of the current theory of biologically activated alkylating agents.
- Mlochowski, Jacek,Kubicz, Elzbieta,Kloc, Krystian,Mordarski, Marian,Peczynska, Wanda,Syper, Ludwik
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p. 455 - 464
(2007/10/02)
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- A NEW METHOD FOR THE OXIDATION OF METHYL TO FORMYL GROUPS IN HETEROAROMATIC DERIVATIVES
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The oxidation of α- and γ-methyl-substituted heteroaromatic bases by t-BuI/DMSO ot I2/t-BuI/DMSO systems leads to the corresponding aldehydes.
- Vismara, Elena,Fontana, Francesca,Minisci, Francesco
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p. 135 - 136
(2007/10/02)
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- REACTIVITY OF METHYL DERIVATIVES OF NITROGENOUS HETEROCYCLES IN VAPOR-PHASE CATALYTIC OXIDATION
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A study has been made of the reactivity of methylpyridines, methylpyrazines, and methylquinolines in oxidation in the vapor phase in the presence of β-VO(PO3)2.Relationships have been found between the overall reaction rates of heterocyclic compounds and the charge on the ring nitrogen, and between the partial oxidation rate and the charge on the ring carbon atom adjacent to the methyl group.The partial oxidation rate of methylpyridines is given to a first approximation by the Hammett-type expression lnWa = -3.5 + 4.6 Σ?, with a correlation coefficient of 0.93.
- Leitis, L. Ya.,Skolmeistere, R. A.,Golender, L. O.,Yansone, D. P.,Meksh, P. A.,Shimanskaya, M. V.
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- CONVERSION OF INDOLES INTO QUINOLINES THROUGH THE N-1-C-2 FISSION BY SINGLET-OXYGEN AS A MODEL EXPERIMENT OF BIOMIMETIC SYNTHESIS OF QUININE ALKALOIDS
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Photo-oxygenation of indole-3-acetaldehydes (28-30) followed by treatments with dimethyl sulphide and then dilute acetic acid gave 4-acylquinolines (13, 31 and 32), respectively.
- Ihara, Masataka,Noguchi, Kazuharu,Fukumoto, Keiichiro,Kametani, Tetsuji
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p. 2109 - 2114
(2007/10/02)
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- PHOTO-OXYGENATION OF INDOLE-3-ACETIC ACIDS AND INDOLE-3-ACETALDEHYDES: BIOMIMETIC CONVERSION OF INDOLES INTO QUINOLINES VIA N1-C2 FISSION
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New conversion of indoles to quinolines via the N1-C2 fission using singlet oxygen reaction was investigated starting from indole-3-acetic acids and indole-3-acetaldehydes.Dye-induced photo-oxydation of indole-3-acetaldehyde derivatives (17 and 18) followed by treatments with dimethyl sulfide and then acetic acid produced 4-formyl- and 4-acetylquinolines (19 and 20), respectively.
- Ihara, Masataka,Noguchi, Kazuharu,Fukumoto, Keiichiro,Kametani, Tetsuji
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p. 421 - 424
(2007/10/02)
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- Oxidation of Benzylic Hydrocarbons with Benzeneseleninic Anhydride and Related Reactions
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The use of benzeneseleninic anhydride as a new side-chain oxidant for a variety of aromatic and heteroaromatic hydrocarbons has been investigated.The oxidation normally proceeds well for simple substrates, neat or in chlorobenzene solution at 100-130 deg C.In examples where the aromatic rings are susceptible towards electrophilic attack selenated compounds are usually formed as the major by-products.
- Barton, Derek H. R.,Hui, Raymond A. H. F.,Ley, Steven V.
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p. 2179 - 2186
(2007/10/02)
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- THE PREPARATION OF ARYLGLYOXALS AND HETEROAROMATIC ALDEHYDES USING PYRIDONA
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Aodium 1-oxido-4,6-diphenyl-2-pyridone reacts with phenacyl halides to give arylglyoxals and with N-heteroarylmethylpyridinium cations to give heteroaromatic aldehydes and ketones.
- Katritzky, A. R.,Chapman, A. V.,Dowlatshahi, H. M.
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p. 315 - 320
(2007/10/02)
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