Beilstein J. Org. Chem.2013,9, 401–405, doi:10.3762/bjoc.9.41
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; Introduction
The intermolecular Huisgen azide–alkyne 1,3-dipolar cycloaddition reaction [1][2][3][4][5][6] for the synthesis of 1,2,3-triazoles in both aqueous [7][8][9][10] and organic solvents under either metal-catalyzed [11][12][13] or metal-free conditions [14][15][16] has received
indolodiazepinotriazoles in good yields.
Results and Discussion
We commenced our studies with the development of a one-pot three-component strategy involving the condensation of the 2-(4-methylphenylethynyl)-1H-indole (1a) with epichlorohydrin (2) and sodium azide (3, Scheme 1, Table 1). Initially, a mixture of 1a, 2 and
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Graphical Abstract
Scheme 1:
One-pot three-component domino reaction furnishing indole derivatives (4a and 5a) and indolodiazepi...