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Beilstein J Org Chem. 2013;9:401-5. doi: 10.3762/bjoc.9.41. Epub 2013 Feb 19.

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

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1
Medicinal & Process Chemistry Division CSIR-Central Drug Research Institute, Lucknow-226001, India.

Abstract

A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide-internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

KEYWORDS:

1,3-dipolar cycloaddition; 2-alkynylindoles; azides; domino reaction; indolodiazepinotriazoles

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