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Regioselectivity of cyclization of 3-allyl(propargyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles

Research paper by R. I. Vasˈkevich, A. I. Vasˈkevich, A. V. Turov, V. I. Staninets, M. V. Vovk

Indexed on: 24 Nov '11Published on: 24 Nov '11Published in: Chemistry of Heterocyclic Compounds



Abstract

The interaction of 3-allylsulfanyl-5H-[1,2,4]triazino[5,6-b]indole with iodine led to 1-iodomethyl-1,2-dihydro[1,3]thiazolo[2',3':3,4][1,2,4]triazino[5,6-b]indol-11-ium pentaiodide with an angular structure, on the basis of which 1-iodomethyl-1,2-dihydro[1,3]thiazolo-, 1-methylidene-1,2-di-hydro[1,3]thiazolo, and 1-methyl[1,3]thiazolo derivatives were obtained. The intramolecular cyclization of 3-propargyl(allyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles under the influence of concentrated sulfuric acid led to linear annelated products:3-methyl[1,3]thiazolo[3',2':2,3][1,2,4]tri-azino[5,6-b]indole or its 2,3-dihydro derivative.