Reactions of 1,2,5-thiadiazole 1,1-dioxide derivatives with nitrogen nucleophiles. Part IV. Addition of Ą-diamines

M. V. MIRÍFICO; J. A. CARAM; E. J. VASINI; O. E. PIRO; E. E. CASTELLANO

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

JOHN WILEY & SONS LTD

Año: 2009 vol. 22 p. 163 - 169

0894-3230

a-diaminesQ2, such as ethylendiamine and o-phenylendiamine, add to 3,4-aryl-disubstituted 1,2,5-thiadiazole 1,1-dioxides to give dihydropyrazines or quinoxalines, respectively and sulfamide. The new compound acenaphtho [5,6-b]-2,3-dihydropyrazine was synthesized and characterized. The addition of ethylendiamine to 3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide gives 3,4-disubstituted thiadiazolidine 1,1-dioxide, dihydropyrazines, or pyrazines, depending on the reaction condition used. The reactions were followed by cyclic voltammetry and NMR spectroscopy which, in some cases, allowed the detection of the thiadiazolidine intermediate. .