Literature DB >> 17576479

Organometallic methods for the synthesis and functionalization of azaindoles.

Jinhua J Song1, Jonathan T Reeves, Fabrice Gallou, Zhulin Tan, Nathan K Yee, Chris H Senanayake.   

Abstract

Azaindoles (also called pyrrolopyridines) constitute essential subunits in many pharmaceutically important compounds. The synthesis of azaindoles has been a great synthetic challenge for chemists. Many classical methods for indole synthesis (such as Fischer and Madelung cyclizations) often cannot be effectively applied to the synthesis of the corresponding azaindoles. In recent years, advances in organometallic chemistry have enabled a number of novel and efficient methodologies for azaindole formation as well as for the further functionalization of azaindole templates. In this tutorial review, we have surveyed the recent development of organometallic chemistry-based methods for azaindole synthesis.

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Year:  2007        PMID: 17576479     DOI: 10.1039/b607868k

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  10 in total

1.  Palladium-catalyzed amination of unprotected halo-7-azaindoles.

Authors:  Jaclyn L Henderson; Sarah M McDermott; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

2.  Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

Authors:  M Alexander Düfert; Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-08-16       Impact factor: 15.419

3.  Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst.

Authors:  Anton A Toutov; Wen-Bo Liu; Kerry N Betz; Alexey Fedorov; Brian M Stoltz; Robert H Grubbs
Journal:  Nature       Date:  2015-02-05       Impact factor: 49.962

4.  Titanocene(III)-catalyzed formation of indolines and azaindolines.

Authors:  Peter Wipf; John P Maciejewski
Journal:  Org Lett       Date:  2008-09-10       Impact factor: 6.005

5.  Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines.

Authors:  Yun Ma; Sean Breslin; Ivan Keresztes; Emil Lobkovsky; David B Collum
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

6.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

7.  Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.

Authors:  Hui-Qi Ni; Ilia Kevlishvili; Pranali G Bedekar; Joyann S Barber; Shouliang Yang; Michelle Tran-Dubé; Andrew M Romine; Hou-Xiang Lu; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  Nat Commun       Date:  2020-12-22       Impact factor: 14.919

8.  Regioselective C-H sulfenylation of N-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles.

Authors:  Jingyan Hu; Xiaoming Ji; Shuai Hao; Mingqin Zhao; Miao Lai; Tianbao Ren; Gaolei Xi; Erbin Wang; Juanjuan Wang; Zhiyong Wu
Journal:  RSC Adv       Date:  2020-08-27       Impact factor: 4.036

9.  Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.

Authors:  Rajendra Surasani; Dipak Kalita; A V Dhanunjaya Rao; K B Chandrasekhar
Journal:  Beilstein J Org Chem       Date:  2012-11-19       Impact factor: 2.883

Review 10.  Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization.

Authors:  A Sofia Santos; Ana C Mortinho; M Manuel B Marques
Journal:  Molecules       Date:  2018-10-17       Impact factor: 4.411

  10 in total

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