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
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3061-3063
- https://doi.org/10.1039/p19790003061
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.This publication has 0 references indexed in Scilit: