21390-88-5Relevant academic research and scientific papers
Silver-catalyzed isocyanide-alkyne cycloaddition: A general and practical method to oligosubstituted pyrroles
Liu, Jianquan,Fang, Zhongxue,Zhang, Qian,Liu, Qun,Bi, Xihe
supporting information, p. 6953 - 6957 (2013/07/25)
Ag2CO3 is the key: The transition-metal-catalyzed cycloaddition of isocyanides and unactivated terminal alkynes has been realized with Ag2CO3 as a unique and robust catalyst (see scheme). The protocol is highly
Synthesis of pyrroles by click reaction: Silver-catalyzed cycloaddition of terminal alkynes with isocyanides
Gao, Meng,He, Chuan,Chen, Hongyi,Bai, Ruopeng,Cheng, Ben,Lei, Aiwen
supporting information, p. 6958 - 6961 (2013/07/25)
Just click with silver: Pyrroles are prepared by the co-cyclization of terminal alkynes and isocyanides in a silver-catalyzed click reaction. This route represents an extremely simple, efficient, and atom-economic approach to substituted pyrroles in good yields with high selectivity, thus complementing the click method for the rapid formation of multifunctional heterocycles. Copyright
Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
Wang, Peiyuan,Naduthambi, Devan,Mosley, Ralph T.,Niu, Congrong,Furman, Phillip A.,Otto, Michael J.,Sofia, Michael J.
scheme or table, p. 4642 - 4647 (2011/09/12)
Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t)ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 μM in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors.
Oligosubstituted pyrroles directly from substituted methyl isocyanides and acetylenes
Lygin, Alexander V.,Larionov, Oleg V.,Korotkov, Vadim S.,De Meijere, Armin
supporting information; experimental part, p. 227 - 236 (2009/06/20)
The formal cycloaddition of α-metallated methyl isocyanides 1 onto the triple bond of electron-deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3. The scope and limitations of this reaction (24 examples, 2597 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed CuI-mediated synthesis of 2,3-disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5-88% yield).
The Preparation of Pyrrole-2-carboxylates from Vinyl Sulfones
Arnold, Dennis P.,Burgess-Dean, Leon,Hubbard, Jason,Rahman, M. Abdur
, p. 969 - 974 (2007/10/02)
The reaction of the anion of ethyl isocyanoacetate with suitably substituted vinyl p-tolyl sulfones gives fair to good yields of pyrrole-2-carboxylates substituted in the 3-, 4- or 3- and 4-positions.From the reaction of 1-phenyl-1-tolylsulfonylethene with ethyl isocyanoacetate, two diastereoisomers of ethyl 4,6-diphenyl-4,6-bis(p-tolylsulfonyl)-3,4,5,6-tetrahydro-2H-azepine-2-carboxylate (4) were also isolated.
Differential Reactivity of β-Amino Enones and 3-Dimethylaminoacrylaldehyde towards α-Amino Derivatives
Alberola, Angel,Andres, Jose M.,Gonzalez, Alfonso,Pedrosa, Rafael,Vicente, Martina
, p. 2681 - 2685 (2007/10/02)
Unsubstituted β-amino enones react with α-amino derivatives by a well established route with implies a fast transamination process - 1,4-addition followed by elimination - and cyclodehydration of the intermediate to 3-functionalized pyrroles.In contrast, 3-dimethylaminoacrylaldehyde undergoes 1,2-addition followed by cyclization to give the final 2-substituted pyrroles.Isolation of the intermediates supports the proposed mechanism for each reaction.
