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

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

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