Azulene-1-azo-2′-thiazoles. Synthesis and properties

✍ Scribed by Alexandru C. Razus; Liviu Birzan; Stefania Nae; Mirela Nina Surugiu; Valentin Cimpeanu

• Book ID: 102341907
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 117 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400607

✦ Synopsis

Abstract

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 HNO~3~/H~3~PO~4~ followed by the coupling of diazonium salts with azulenes in buffered medium. The reactions proved to be general for this class, the yields are, however, considerably 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 intrinsic properties of thiazole moiety.