A novel reaction of 2-phenacyl mercaptoimidazole with acetic anhydride: formation of an imidazothiazole with loss of a phenyl group

Autor: Shashiprabha, Suresh P. Nayak, K Sundarraja Rao, K Shridhara, Kuppuswamy Nagarajan, T. N. Guru Row, Sajesh P. Thomas
Rok vydání: 2020
Předmět:
Zdroj: Journal of Chemical Sciences. 132
ISSN: 0973-7103
0974-3626
DOI: 10.1007/s12039-020-01824-y
Popis: Attempted cyclodehydration of phenacyl mercaptoimidazole hydrobromide with acetic anhydride gave an abnormal product lacking the phenyl group. The molecular structure is confirmed using X-ray crystal structure studies. Phenacyl mercaptobenzimidazole hydrobromide behaved similarly. Analysis of crystal structure revealed an intermolecular S…Br chalcogen bonding interaction. The cylization reaction of 2-phenacylmercaptoimidazole hydrobromide is carried out using acetic anhydride, afforded an unexpected imidazothiazole lacking a phenyl ring. The generality of the reaction is confirmed by a similar reaction which was carried out with phenacylmercaptobenzimidazole and yielded similar product
Databáze: OpenAIRE