Literature DB >> 27363788

Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes.

Hayden A Sharma1, M Todd Hovey, Karl A Scheidt.   

Abstract

A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

Entities:  

Year:  2016        PMID： 27363788      PMCID： PMC4950954          DOI： 10.1039/c6cc04735a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  33 in total

1.  Design and synthesis of 4-azaindoles as inhibitors of p38 MAP kinase.

Authors:  Alejandra Trejo; Humberto Arzeno; Michelle Browner; Sushmita Chanda; Soan Cheng; Daniel D Comer; Stacie A Dalrymple; Pete Dunten; JoAnn Lafargue; Brett Lovejoy; Jose Freire-Moar; Julie Lim; Joel Mcintosh; Jennifer Miller; Eva Papp; Deborah Reuter; Rick Roberts; Florentino Sanpablo; John Saunders; Kyung Song; Armando Villasenor; Stephen D Warren; Mary Welch; Paul Weller; Phyllis E Whiteley; Lu Zeng; David M Goldstein
Journal:  J Med Chem       Date:  2003-10-23       Impact factor: 7.446

2.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

Review 3.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

4.  Discovery of novel heterocyclic factor VIIa inhibitors.

Authors:  Roopa Rai; Aleksandr Kolesnikov; Paul A Sprengeler; Steven Torkelson; Tony Ton; Bradley A Katz; Christine Yu; John Hendrix; William D Shrader; Robin Stephens; Ronnell Cabuslay; Ellen Sanford; Wendy B Young
Journal:  Bioorg Med Chem Lett       Date:  2006-02-03       Impact factor: 2.823

5.  N-heterocyclic carbenes as organocatalysts.

Authors:  Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

Authors:  M Todd Hovey; Christopher T Check; Alexandra F Sipher; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

7.  Structure-activity relationships of a series of pyrrolo[3,2-d]pyrimidine derivatives and related compounds as neuropeptide Y5 receptor antagonists.

Authors:  M H Norman; N Chen; Z Chen; C Fotsch; C Hale; N Han; R Hurt; T Jenkins; J Kincaid; L Liu; Y Lu; O Moreno; V J Santora; J D Sonnenberg; W Karbon
Journal:  J Med Chem       Date:  2000-11-02       Impact factor: 7.446

8.  Organocatalytic C-H bond arylation of aldehydes to bis-heteroaryl ketones.

Authors:  Qiao Yan Toh; Andrew McNally; Silvia Vera; Nico Erdmann; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2013-02-27       Impact factor: 15.419

9.  Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis.

Authors:  Vijay Nair; Sreekumar Vellalath; Beneesh Pattoorpadi Babu
Journal:  Chem Soc Rev       Date:  2008-10-21       Impact factor: 54.564

Review 10.  The azaindole framework in the design of kinase inhibitors.

Authors:  Jean-Yves Mérour; Frédéric Buron; Karen Plé; Pascal Bonnet; Sylvain Routier
Journal:  Molecules       Date:  2014-11-28       Impact factor: 4.411
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