Literature DB >> 22085027

Three-component tandem reaction involving acid chlorides, terminal alkynes, and 2-aminoindole hydrochlorides: synthesis of α-carboline derivatives in aqueous conditions via regioselective [3 + 3] cyclocondensation.

Sahaj Gupta1, Brijesh Kumar, Bijoy Kundu.   

Abstract

An efficient synthesis toward highly diversified α-carboline derivatives via a three-component tandem reaction using acid chlorides, terminal alkynes, and 2-aminoindole hydrochlorides has been described. The salient feature of the one-pot strategy involves regioselective [3 + 3]-cyclocondensation and the presence of water in the reaction medium to facilitate cyclization. Nonaqueous conditions furnished products in poor yields.

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Year:  2011        PMID: 22085027     DOI: 10.1021/jo201994v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization.

Authors:  Piyush Kumar Agarwal; Meena Devi Dathi; Mohammad Saifuddin; Bijoy Kundu
Journal:  Beilstein J Org Chem       Date:  2012-11-08       Impact factor: 2.883

3.  Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles.

Authors:  Rajesh K Arigela; Sudhir K Sharma; Brijesh Kumar; Bijoy Kundu
Journal:  Beilstein J Org Chem       Date:  2013-02-19       Impact factor: 2.883

4.  A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes.

Authors:  Sophie J Markey; William Lewis; Christopher J Moody
Journal:  Org Lett       Date:  2013-11-26       Impact factor: 6.005

  4 in total

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