Beilstein J. Org. Chem.2013,9, 401–405, doi:10.3762/bjoc.9.41
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
azide–internal alkyne 1,3-dipolar cycloaddition reaction.
Once the reaction conditions for the three-component format had been optimized, several 2-alkynylindoles bearing different functional groups were treated with epichlorohydrin and sodium azide in order to establish the scope and limitation of the
PDF
Graphical Abstract
Scheme 1:
One-pot three-component domino reaction furnishing indole derivatives (4a and 5a) and indolodiazepi...
Beilstein J. Org. Chem.2011,7, 1387–1406, doi:10.3762/bjoc.7.163
step. Xi and co-workers developed an elegant one-pot synthesis of 2-alkynylindoles 64 involving o-bromo-(2,2-dibromovinyl)benzenes 63, arylamines and terminal alkynes as starting partners [36]. It should be noted that the three components are present at the same time in the reaction system and the best
coupling leading to a mono-alkynylated product, followed by an intermolecular Buchwald–Hartwig amination and a subsequent intramolecular amination. This Pd-catalyzed tandem coupling reaction allows the preparation of a variety of 2-alkynylindoles 64 (Scheme 28).
An elegant three-component process based on