Issue 0, 1979

Reactions of tryptophols and Nα-acetyltryptamines with iodine azide. Formation of 3a-azido-3,3a,8,8a-tetrahydro-2H-furo- and 3a-azido-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indoles

Abstract

Reaction of 2-methyltryptophol (1a) with 1 molar equivalent of iodine azide gives 3a-azido-8a-methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole, which isomerises to 2-azidomethyltryptophol in acetic acid at room temperature. Similar treatment of Nα-acetyl-2-methyltryptamine affords two products, 1-acetyl-3a-azido-8a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole and Nα-acetyl-2-azidomethyltryptamine; the former does not isomerise to the latter in acetic acid. Tryptophol and Nα-acetyltryptamine also give the corresponding 3a-azidofuro and -pyrrolo-indole derivatives in low yields.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 3061-3063

Reactions of tryptophols and Nα-acetyltryptamines with iodine azide. Formation of 3a-azido-3,3a,8,8a-tetrahydro-2H-furo- and 3a-azido-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indoles

M. Ikeda, K. Ohno, M. Katsura, M. Chun and Y. Tamura, J. Chem. Soc., Perkin Trans. 1, 1979, 3061 DOI: 10.1039/P19790003061

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