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

Abstract

3-(3-Chloroprop-2-en-1-ylsulfanyl)and 3-(prop [5,6-b]indoles reacted with iodine and bromine to give derivatives of 2,3-dihydro-10H-[1,3]thiazolo[3′,2′ : 2,3][1,2,4]triazino[5,6-b]indolium halides whose structure was determined by 1 H and 13 C NMR spectroscopy using twodimensional 1 H-1 H COSY, 1 H-13 C HSQC, and 1 H-13 C HMBC techniques.

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

“…In the literature [16] there are data for alkylation in tetrahydrofuran of 5-phenyl-2,3-dihydro-1,2,4triazine-3-thione (1) by benzyl, butenyl, and butynyl halides, proceeding at the sulfur atom. Heterocyclization of 3-allylsulfanyl- [17], 3-cinnamylsulfanyl-5phenyl-1,2,4-triazine [18], as well as 3-alkenylsulfanyl- [19] and 3-propargylsulfanyl-5H- [1,2,4]triazino [5,6b]indoles [20] under the action of halogens progresses with participation of the N-2 nitrogen atom of the triazine cycle producing thiazolo(thiazino) [3,2-b][1,2,4]triazine systems. In the present study in an effort to obtain new annulated heterocyclic systems 3-propargylsulfanyl-5-phenyl-1,2,4-triazine (2) has been synthesized for the first time, and its interaction with halogens has been investigated.…”