Literature DB >> 28281340

Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Gerardo X Ortiz1, Brett N Hemric1, Qiu Wang1.   

Abstract

Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

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Year:  2017        PMID： 28281340      PMCID： PMC5685508          DOI： 10.1021/acs.orglett.7b00358

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Facile synthesis of N-dialkylaminomethyl-substituted heterocycles.

Authors:  Brian E Love
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

2.  Mild and selective Ru-catalyzed formylation and Fe-catalyzed acylation of free (N-H) indoles using anilines as the carbonyl source.

Authors:  Wenliang Wu; Weiping Su
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

3.  New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.

Authors:  E Arzel; P Rocca; P Grellier; M Labaeïd; F Frappier; F Guéritte; C Gaspard; F Marsais; A Godard; G Quéguiner
Journal:  J Med Chem       Date:  2001-03-15       Impact factor: 7.446

4.  An annulative electrophilic amination approach to 3-aminobenzoheteroles.

Authors:  Naoki Matsuda; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal:  J Org Chem       Date:  2011-12-15       Impact factor: 4.354

5.  Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three Component Coupling Reaction.

Authors:  Dmitri Chernyak; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2010-04-19       Impact factor: 5.837

6.  A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

Authors:  T Okauchi; M Itonaga; T Minami; T Owa; K Kitoh; H Yoshino
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

7.  Regioselective synthesis of 3-alkylindoles mediated by zinc triflate.

Authors:  Xiuwen Zhu; A Ganesan
Journal:  J Org Chem       Date:  2002-04-19       Impact factor: 4.354

8.  Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles.

Authors:  Tao-Shan Jiang; Guan-Wu Wang
Journal:  Org Lett       Date:  2013-01-25       Impact factor: 6.005

9.  N-Amination of pyrrole and indole heterocycles with monochloramine (NH2Cl).

Authors:  John Hynes; Wendel W Doubleday; Alaric J Dyckman; Jollie D Godfrey; John A Grosso; Susanne Kiau; Katerina Leftheris
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354

10.  Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Taradas Sarkar; Maria Dora Carrion; Carlota Lopez Cara; Olga Cruz-Lopez; Delia Preti; Mojgan Aghazadeh Tabrizi; Manlio Tolomeo; Stefania Grimaudo; Antonella Di Cristina; Nicola Zonta; Jan Balzarini; Andrea Brancale; Hsing-Pang Hsieh; Ernest Hamel
Journal:  J Med Chem       Date:  2008-02-09       Impact factor: 7.446
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  2 in total

1.  A Simple and Broadly Applicable C-N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents.

Authors:  Xiaofeng Ma; Joshua J Farndon; Tom A Young; Natalie Fey; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

2.  The hydrogen atom transfer reactivity of sulfinic acids.

Authors:  Markus Griesser; Jean-Philippe R Chauvin; Derek A Pratt
Journal:  Chem Sci       Date:  2018-07-31       Impact factor: 9.825
  2 in total

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