A Facile Synthesis of 3‐(Arylthio)imidazo[1, 2‐a]pyridin‐2(3H)‐ones from 2‐Aminopyridinium Bromides and Sodium Arenesulfinates. Issue 45 (23rd November 2020)

• Record Type: Journal Article
• Authors: Saroj, ; Rangan, Krishnan; Kumar, Anil
• Is Part Of: European journal of organic chemistry. Issue 45(2020)
• Page Start: 7015
• Page End: 7022
• Publication Date: 2020-11-23
• Subjects: 2‐Aminopyridinium salt -- Amidation -- Cyclization -- Imidazo[1, 2‐a]pyridine‐2(3H)one -- Sulfenylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000996
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A simple and convenient method has been developed for the synthesis of 3‐(arylthio)imidazo[1, 2‐ a ]pyridin‐2(3H)‐ones through a catalyst‐free reaction of 2‐aminopyridinium bromides with sodium arenesulfinates. A variety of 3‐(arylthio)imidazo[1, 2‐ a ]pyridin‐2(3H)‐ones were obtained in moderate to excellent (33–85 %) yields. The developed protocol is operationally simple, exhibits a broad substrate scope with a wide range of functional groups, and is amenable for gram‐scale synthesis. Abstract : Synthesis of 3‐(arylthio)imidazo[1, 2‐ a ]pyridin‐2(3H)‐ols has been achieved through a catalyst‐free, one‐pot reaction of 2‐aminopyridinium bromides with sodium arenesulfinates. The tandem reaction involved intramolecular amidation followed by sulfenylation and afforded a wide range of 3‐(arylthio)imidazo[1, 2‐ a ]pyridin‐2(3H)‐ols in moderate to excellent (33–85 %) yields. The method exhibited broad substrate scope with a wide range of functional group tolerance, and is amenable for gram‐scale synthesis.