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Reactions of 1,2,5‐thiadiazole 1,1‐dioxide derivatives with nitrogen nucleophiles. Part IV. Addition of α ‐diamines
Author(s) -
Mirífico María Virginia,
Caram José Alberto,
Vasini Enrique Julio,
Piro Oscar Enrique,
Castellano Eduardo E.
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1444
Subject(s) - chemistry , sulfamide , nucleophile , nitrogen dioxide , aryl , nitrogen , medicinal chemistry , organic chemistry , catalysis , alkyl
α ‐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. Copyright © 2008 John Wiley & Sons, Ltd.