- Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
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A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.
- Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet
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supporting information
p. 1847 - 1856
(2021/04/26)
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- Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
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A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.
- Zeng, Ge,Liu, Jichao,Shao, Yinlin,Zhang, Fangjun,Chen, Zhongyan,Lv, Ningning,Chen, Jiuxi,Li, Renhao
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p. 861 - 867
(2021/01/09)
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- Method for synthesizing beta-ketonitrile and derivatives thereof
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The invention discloses a method for synthesizing beta-ketonitrile and derivatives thereof. The beta-ketonitrile is prepared by a reaction of malononitrile and derivatives thereof with arylboronic acid. According to the invention, reactants are wide in source and low in cost; the reaction is carried out in a solvent, and the solvent is a mixture of toluene and water; in the process of the reaction, a palladium catalyst, an acid additive and a ligand are also added into the solvent; the acidic additive is any one selected from benzenesulfonic acid, p-toluenesulfonic acid, p-nitrobenzenesulfonic acid, trifluoromethanesulfonic acid and trifluoroformic acid; and the ligand is any one selected from 4,4'-dimethyl-2,2'-bipyridyl, 6,6'-dimethyl-2,2'-bipyridyl and 5,5'-dimethyl-2,2'-bipyridyl. The method in the invention can directly synthesize the target product in one step, does not need to separate an intermediate product, can obtain the target product only by a stirring reaction under normal pressure, has the highest yield of 98%, is especially suitable for synthesis of beta-ketonitrile derivatives sensitive to alkaline conditions, and provides better guarantee for development of organic compounds related to beta-ketonitrile derivatives.
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Paragraph 0061-0065
(2021/04/21)
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- One-pot synthesis of dual-state emission (DSE) luminogens containing the V-shape furo[2,3-b]furan scaffold
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To discover novel fluorophores of solution and solid dual-state emission (DSE) materials, unique V-shape furo[2,3-b]furans have been designed and synthesized by a one-pot method for the first time and their photoluminescent properties have been explored in benzene, THF, DMF and DMSO, as well as in the solid state. As the best example, 2,5-bis(4-(9H-carbazol-9-yl)phenyl)-6a-amino-3a,6a-dihydrofuro[2,3-b]furan-3,3a,4-tricarbonitrile (3g) exhibited solution and solid DSE properties in THF, benzene, and in the solid state with quantum yields of 55%, 92%, and 45%, respectively.
- Zhou, Jie,Huang, Manna,Zhu, Xinhai,Wan, Yiqian
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supporting information
p. 445 - 448
(2020/03/11)
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- Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center
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A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.
- Liu, Chong,Yuan, Jing,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin
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supporting information
p. 8997 - 9002
(2021/03/16)
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- One-Pot Four-Component Coupling Approach to Polyheterocycles: 6 H-Furo[3,2- f]pyrrolo[1,2- d][1,4]diazepine
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A novel polyheterocyclic chemical space, 6H-furo[3,2-f]pyrrolo[1,2-d][1,4]diazepine, was generated by a one-pot four-component coupling reaction where multiple bonds (three C-C, one C-O, and one C-N) were formed through a domino sequence. Two heterocyclic rings (furan and diazepine) were sequentially constructed from the monocyclic pyrrole derivative under environment-friendly reaction conditions to furnish the tricyclic fused scaffold.
- Yoon, Seok Hyun,Kim, Sung June,Kim, Ikyon
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p. 15082 - 15091
(2020/12/02)
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- Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation–Amidation Reaction
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AN oxidative decyanation–amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reactio
- Zhang, Ya-Kai,Wang, Bin
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supporting information
p. 5732 - 5735
(2019/08/27)
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- Rh(III)-Catalyzed C-H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo [de] chromenes
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Rh (III)-catalyzed C-H activation of benzoylacetonitriles in coupling with diazo compounds was developed to synthesize diversified substituted benzo[de]chromenes via a formal (4 + 2) cycloaddition with a diazo compound and subsequent tandem (4 + 2) cycloa
- Fang, Feifei,Zhang, Chunmei,Zhou, Chaofan,Li, Yazhou,Zhou, Yu,Liu, Hong
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supporting information
p. 1720 - 1724
(2018/04/14)
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- Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides
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A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling. (Chemical Equation Presented).
- Jensen, Mikkel T.,Juhl, Martin,Nielsen, Dennis U.,Jacobsen, Mikkel F.,Lindhardt, Anders T.,Skrydstrup, Troels
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p. 1358 - 1366
(2016/03/01)
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- Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides
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A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is
- Mamuye, Ashenafi Damtew,Castoldi, Laura,Azzena, Ugo,Holzer, Wolfgang,Pace, Vittorio
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supporting information
p. 1969 - 1973
(2015/03/05)
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- Specific 1,2-Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β-Ketonitriles
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A series of β-ketonitriles was synthesized within 30 min under mild conditions through the BF3 ·OEt2-catalyzed addition reactions of diazoacetonitrile to aromatic aldehydes and subsequent 1,2-hydride shift. This method is advantageous in that it is operationally simple, mild and metal-free conditions are used, the substrate scope is wide, and the products are obtained in moderate to high yields (up to 81 %). Additionally, γ,δ-unsaturated β-ketonitriles are also accessible by this method by using cinnamaldehydes.
- Yang, Zhanhui,Son, Kwon-Il,Li, Siqi,Zhou, Bingnan,Xu, Jiaxi
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supporting information
p. 6380 - 6384
(2016/02/18)
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- A novel class of AMPA receptor allosteric modulators. Part 1: Design, synthesis, and SAR of 3-aryl-4-cyano-5-substituted-heteroaryl-2-carboxylic acid derivatives
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The synthesis and initial SAR studies of novel, highly potent positive allosteric modulators of AMPA receptors based on 3-(4-tert-butylphenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid (6a) are described. SAR studies at the thioether moiety ind
- Fernandez, Maria-Carmen,Castano, Ana,Dominguez, Esteban,Escribano, Ana,Jiang, Delu,Jimenez, Alma,Hong, Eric,Hornback, William J.,Nisenbaum, Eric S.,Rankl, Nancy,Tromiczak, Eric,Vaught, Grant,Zarrinmayeh, Hamideh,Zimmerman, Dennis M.
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p. 5057 - 5061
(2007/10/03)
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- ARALKYL AMINES AS CANNABINOID RECEPTOR MODULATORS
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Novel compounds of the structural formula (I) are antagonists and/or inverse agonists of the Cannabinoid-1 (CB1) receptor and are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. The compounds of the present invention are useful as centrally acting drugs in the treatment of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders including multiple sclerosis and Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis, cerebral vascular accidents, and head trauma, anxiety disorders, stress, epilepsy, Parkinson’s disease, movement disorders, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, including alcohol and nicotine addiction, the treatment of obesity or eating disorders, as well as the treatment of asthma, constipation, chronic intestinal pseudo-obstruction, and cirrhosis of the liver.
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Page/Page column 95-96
(2010/02/11)
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- Synthesis and biological effects of a new series of 2-amino-3-benzoylthiophenes as allosteric enhancers of A1-adenosine receptor
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New derivatives of PD 81,723, an allosteric enhancer of agonist binding to the A1-adenosine receptor, have been synthesized and evaluated in an intact cell assay. Compounds 3a, 3o and 3p appeared to be more potent than PD 81,723 and at a concentration of 0.1 μM caused significant reductions of cAMP content of CHO cells expressing the human A1-adenosine receptor. Compounds 4e and 4o appeared to be allosteric enhancers at a low concentration and antagonists at a higher concentration, whereas compounds 3c, 3g, 3s and 4l appeared to be weak antagonists that are also allosteric enhancers at the higher concentration of 10 μM. (C) 2000 Elsevier Science Ltd.
- Baraldi, Pier Giovanni,Zaid, Abdel Naser,Lampronti, Ilaria,Fruttarolo, Francesca,Pavani, Maria Giovanna,Tabrizi, Mojgan Aghazadhe,Shryock, John C.,Leung, Edward,Romagnoli, Romeo
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p. 1953 - 1957
(2007/10/03)
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