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

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 crysta...

Full description

Saved in:
Bibliographic Details
Published in:Journal of chemical sciences (Bangalore, India) India), 2020-12, Vol.132 (1), Article 120
Main Authors: Shashiprabha, Nagarajan, K, Thomas, Sajesh P, Nayak, Suresh P, Rao, K Sundarraja, Shridhara, K, Row, T N Guru
Format: Article
Language:English
Subjects:
Anhydrides
Chalcogen bonds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Crystal structure
Mercaptobenzimidazole
Molecular structure
Regular Article
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Graphic abstract 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
ISSN:0974-3626
0973-7103
DOI:10.1007/s12039-020-01824-y