Issue 0, 1984

[2,3] Fused indoles. Synthesis of β-carbolines and azepino[4,5-b]indoles from 3-(2-alkylindol-3-yl)-2-azidoacrylates1

Abstract

Decomposition of the azidoacrylates (6) derived from 2-substituted indole-3-carbaldehydes gives pharmacologically important β-carbolines [(8), (11)], azepino[4,5-b]indoles (13), or enamines (14) depending on the conditions. The formation of azepinoindoles, shown to proceed by cyclisation of the initially formed enamines, represents a new reaction of vinyl azides which is particularly favoured in the indole series.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2895-2901

[2,3] Fused indoles. Synthesis of β-carbolines and azepino[4,5-b]indoles from 3-(2-alkylindol-3-yl)-2-azidoacrylates1

C. J. Moody and J. G. Ward, J. Chem. Soc., Perkin Trans. 1, 1984, 2895 DOI: 10.1039/P19840002895

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