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Azulene-1-azo-2’-thiazoles. Synthesis and Properties

Domenii publicaţii > Chimie + Tipuri publicaţii > Articol în revistã ştiinţificã

Autori: A. C. Razus, L. Birzan, S. Nae, M. N. Surugiu and V. Cimpeanu

Editorial: Journal of Heterocyclic Chemistry, 40, p.995-1004, 2003.


Several derivatives belonging to a new compound class, namely azulene-1-azo-2′-thiazoles, were prepared by the diazotization of 2-aminothiazoles in the presence of HNO3/H3PO4 followed by the couping o diazonium salts with azulene in buffered medium. The reactions proved to be general for this class, the yields are, however, considerabely influenced by the substituents at thiazole moiety. For the first time a N-oxide provided from an amino substituted five-member nitrogenous heterocycle was diazotized and coupled. The structure of the obtained compounds was assigned and their physico-chemical properties were discussed. The new azulene azo derivatives exhibit a strong bathochromic shift in UV-Vis due to the intense push-pull effect of aromatic system and to the intrinsec properties of thiazole moiety.

Cuvinte cheie: azulene, cuplarea azo, tiazol // azulene, azo coupling, thiazole