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Dithiocarbamates, Thiocarbamic Esters, Dithiocarboimidates, Guanidines, Thioureas, Isothioureas, and Tetraazathiapentalene Derived from 2‐Aminobenzothiazole
Author(s) -
Téllez Fabiola,
Cruz Alejandro,
LópezSandoval Horacio,
RamosGarcía Iris,
Gayosso Martha,
CastilloSierra R. Nely,
PazMichel Brenda,
Nöth Heinrich,
FloresParra Angelina,
Contreras Rosalinda
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400305
Subject(s) - chemistry , dithiocarbamate , hypervalent molecule , sulfur , thiourea , tautomer , guanidine , alkyl , medicinal chemistry , molecule , conformational isomerism , lewis acids and bases , organic chemistry , stereochemistry , catalysis , iodine
Reactions between CS 2 and the exocyclic amino groups of 2‐aminobenzothiazoles gave series of molecules bearing thiourea, isothiourea, dithiocarbamate, dithiocarboimine, dimethyldithiocarbamate, methyldithiocarbamate, S ‐CH 3 and O ‐alkyl thiocarbamic ester, and guanidine groups. Preferred tautomers and conformers were determined. Most compounds present coordinative bonds between the endocyclic sulfur atom, which behaves as a Lewis acid, and oxygen, nitrogen, and sulfur acting as bases. A new dibenzothiazolyltetraazathiapentalene containing a T‐shaped hypervalent sulfur atom and displaying “single bond‐no bond resonance” is discussed. X‐ray structures of eleven compounds are reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)