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The addition reaction of diamides to 1,2,5‐thiadiazole 1,1‐dioxide derivatives
Author(s) -
Caram José A.,
Mirífico María V.,
Aimone Silvia L.,
Piro Oscar E.,
Castellano Eduardo E.,
Vasini Enrique J.
Publication year - 2004
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.829
Subject(s) - chemistry , thiourea , nucleophile , sulfamide , medicinal chemistry , reagent , nitrogen dioxide , ring (chemistry) , urea , organic chemistry , catalysis
The reactions of several derivatives of 1,2,5‐thiadiazole 1,1‐dioxide [3,4‐diphenyl‐( 1a ), 3,4‐bis( p ‐methoxyphenyl)‐( 1b ), phenanthro[9,10‐ c ]‐( 1c ) and acenaphtho[1,2‐c]‐1,2,5‐thiadiazole 1,1‐dioxide ( 1d ), 3,4‐diphenyl‐1,2,5‐thiadiazoline 1,1‐dioxide ( 2a ) and 4‐ethoxy‐5‐methyl‐3,4‐diphenyl‐1,2,5‐thiadiazoline 1,1‐dioxide ( 2b )], with reagents possessing two nucleophilic nitrogen atoms (urea, N , N ′‐dimethylurea, thiourea, N ‐methylthiourea, N ‐ethylthiourea, N ‐allylthiourea, N , N ′‐diethylthiourea, N , N ′‐diphenylthiourea, dithioxamide and sulfamide), were followed by cyclic voltammetry (CV) and UV–visible spectrophotometry in aprotic solvent solution. The products were isolated, characterized by IR, 1 H NMR and 13 C NMR methods and their structure was confirmed by single‐crystal x‐ray diffraction. Several substrate–nucleophile combinations ( 1a – d and 2a with some ureas and thioureas) reacted to give good yields of new compounds formed by the addition reaction of the two nitrogen atoms of the nucleophile to the two >CN— double bonds of the 1,2,5‐thiadiazole 1,1‐dioxide ring. Some systems ( 1a –dithioxamide and 2b –thiourea) did not react, whereas in others (e.g. 1a –sulfamide) a monoaddition equilibrium reaction was observed. Copyright © 2004 John Wiley & Sons, Ltd.