A novel and facile synthesis of 3, 5-Disubstituted isothiozoles under metal free conditions using acetophenones and dithioesters. Issue 17 (1st September 2020)

• Record Type: Journal Article
• Authors: Nagaraju, Chaithra; Ashok, Swarup Hassan; Shamanth, Sadashivamurthy; Nagarakere, Sandhya C.; Sunilkumar, Makanahalli P.; Subbegowda, Rangappa Kanchugarakoppal; Mantelingu, Kempegowda
• Is Part Of: Synthetic communications. Volume 50:Issue 17(2020)
• Page Start: 2647
• Page End: 2654
• Publication Date: 2020-09-01
• Subjects: Air oxidation -- C–N and N–S bond formation -- intramolecular cyclization -- isothiazoles -- metal and catalyst free; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1748656
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: A facile and conveniently simple new protocol is devised for the synthesis of 3, 5-disubstituted and annulated isothiozoles under transition metal and catalyst free conditions utilizing easily available acetophenones, dithioesters and NH4 OAc. This strategy involves C=O and C=S functionalization via sequential imine formation followed by intra molecular cyclization and aerial oxidation forming consecutive C−N and S−N bonds respectively in one pot. This protocol offers a low cost, user friendly, straight forward and widely applicable approach to 3, 5-disubstituted isothiazoles. Graphical Abstract: