Tetrahedron letters

Why are benzimidazoles efficiently acylated with esters? Identification of a tetrahedral hemiacetal alkoxide intermediate

…, C Kadowaki, S Karady, S Kii, K Maeda, BF Marcune…

Index: Asakawa, Ken-Ichi; Dannenberg; Fitch, Kenneth J.; Hall, Stan S.; Kadowaki, Chie; Karady, Sandor; Kii, Satoshi; Maeda, Kenji; Marcune, Benjamin F.; Mase, Toshiaki; Miller, Ross A.; Reamer, Robert A.; Tschaen, David M. Tetrahedron Letters, 2005 , vol. 46, # 30 p. 5081 - 5084

Full Text: HTML

Citation Number: 14

Abstract

Substituted benzimidazoles are important intermediates for the synthesis of various drugs and natural products. Substituents at the 2-position are generally introduced by reaction of the 2-lithio derivative of N-protected benzimidazoles with electrophiles. 1 The dimethoxymethyl N-protecting group has been used because of its easy removal and ketones were obtained by acylation of the corresponding carbanion. 2 In some cases when esters were used as acylating ...

Related Articles:

Room Temperature Palladium??Catalyzed Decarboxylative Acyl/Aroylation using [Fe (III)(EDTA)(η2??O2)] 3− as Oxidant at Biological pH

[Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K. Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678]

X-ray crystal structure and reactions of 2-Cyano-1, 3-dibenzoyl-2, 3-dihydrobenzimidazole, a novel reissert compound.

[Jois, Yajnanarayana H. R.; Berg, Michael A. G.; Merola, Joseph S.; Gibson, Harry W. Tetrahedron Letters, 1991 , vol. 32, # 26 p. 2997 - 3000]

Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1, 2-diamines

[Lian, Mi; Li, Qi; Zhu, Yanping; Yin, Guodong; Wu, Anxin Tetrahedron, 2012 , vol. 68, # 47 p. 9598 - 9605]

Metal-free aerobic oxidation of benzazole derivatives

[Dos Santos, Aurelie; El Kaim, Laurent; Grimaud, Laurence Organic and Biomolecular Chemistry, 2013 , vol. 11, # 20 p. 3282 - 3287]

The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors

[Kim, Moon H.; Tsuhako, Amy Lew; Co, Erick W.; Aftab, Dana T.; Bentzien, Frauke; Chen, Jason; Cheng, Wei; Engst, Stefan; Goon, Levina; Klein, Rhett R.; Le, Donna T.; Mac, Morrison; Parks, Jason J.; Qian, Fawn; Rodriquez, Monica; Stout, Thomas J.; Till, Jeffrey H.; Won, Kwang-Ai; Wu, Xiang; Michael Yakes; Yu, Peiwen; Zhang, Wentao; Zhao, Yeping; Lamb, Peter; Nuss, John M.; Xu, Wei Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 15 p. 4979 - 4985]

More Articles...