Direction of the heterocyclization reaction of 3-allyl- and 3-propargyl-sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles

Reactions of 3-(3-chloroprop-2-en-1-ylsulfanyl)- and 3-(prop-2-yn-1-ylsulfanyl)-5H-[1,2,4]triazino[5,6-b]indoles with halogens

“…Compound 1 reacted with bromine to give 3-(bromochloromethyl)-2,3-dihydro-10H- [1,3]thiazolo[3′,2′:2,3]- [1,2,4]triazino [5,6-b]indolium bromide (5) (Scheme 2) whose structure was confirmed by the 1 H and 13 C NMR spectra, including 1 H-13 C HSQC and HMBC experiments. Among sp 3 -carbon signals in the 13 C NMR spectrum of 5, the most downfield signal (δ C 71.65 ppm) corresponds to the N + CH carbon atom.…”

“…Halocyclizations of 3-allylsulfanyl-5H- [1,2,4]triazino- [5,6-b]indole involve the N 2 atom with formation of [1,3]thiazolo[3′,2′:2,3] [1,2,4]triazino [5,6-b]indole systems [3,4].…”

“…We were the first to study the reactions of 3-(3-chloroprop-2-en-1-ylsulfanyl)-5H- [1,2,4]triazino- [5,6-b]indole (1) and 3-(prop-2-yn-1-ylsulfanyl)-5H- [1,2,4]triazino [5,6-b]indole (2) with bromine and iodine with the goal of obtaining new potentially biologically active thiazolotriazinoindoles. Compound 1 was synthesized in two ways (Scheme 1), by alkylation of 5H- [1,2,4]triazino [5,6-b]indole-3-thione (3) with 1,3-dichloropropene in the system KOH-H 2 O-DMSO (yield 59%) and by one-pot procedure [3] from isatin 3-thiosemicarbazone (4) (yield 29%).…”

“…Compound 1 was synthesized in two ways (Scheme 1), by alkylation of 5H- [1,2,4]triazino [5,6-b]indole-3-thione (3) with 1,3-dichloropropene in the system KOH-H 2 O-DMSO (yield 59%) and by one-pot procedure [3] from isatin 3-thiosemicarbazone (4) (yield 29%). The 1 H NMR spectrum of 1 contained two sets of signals with equal intensities, indicating that the product was a 1 : 1 mixture of cis and trans isomers.…”

Halocyclization of 3-{[2-methyl(bromo)prop-2-en-1-yl]-sulfanyl}-5H-[1,2,4]triazino[5,6-b]indoles

“…Halocyclization of 3-(allylsulfanyl)-5H- [1,2,4]triazino [5,6-b]indole (1) is known to afford five-membered thiazole ring linearly fused to the triazinoindole system [5]. In this work we describe the reactions of 3-(2-bromoprop-2-en-1-yl)sulfanyl]-5H- [1,2,4]triazino- [5,6-b]indole (2) and 3-[(2-methylprop-2-en-1-yl)sulfanyl]-5H- [1,2,4]triazino [5,6-b]indole (3) with iodine and bromine.…”