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

MARÍA VIRGINIA MIRÍFICO *; JOSÉ ALBERTO CARAM; ENRIQUE JULIO VASINI; OSCAR ENRIQUE PIRO; EDUARDO E. CASTELLANO

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

JOHN WILEY & SONS LTD

Lugar: Chichester. England; Año: 2009 vol. 22 p. 163 - 169

0894-3230

-diamines, 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.