Reagent‐Controlled Chemodivergent Approach to Thiazolines and Thiazines from α‐N‐Hydroxyimino Dithioesters. Issue 18 (6th September 2022)

• Record Type: Journal Article
• Authors: Ray, Subhasish; Singh, Saurabh; Kumar, Ganesh; Shukla, Gaurav; Shankar Singh, Maya
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 18(2022)
• Page Start: 3204
• Page End: 3210
• Publication Date: 2022-09-06
• Subjects: α-N-Hydroxyimino-β-oxodithioesters -- 2-Chloroethylamine hydrochloride/3-Chloropropylamine hydrochloride -- Thiazolines -- Thiazines -- Chemoselectivity -- Intramolecular Cyclization; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200511
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A chemoselective route to thiazolines and thiazines has been devised by heterocyclization of viable α‐N‐hydroxyimino‐β‐oxodithioesters with 2‐chloroethylamine hydrochloride/3‐chloropropylamine hydrochloride, which does not require metals or additives and proceeds at 0–60 °C. The overall transformation involves base mediated intramolecular cyclization of α‐N‐hydroxyimino‐β‐oxodithioesters to 4‐membered oxazete‐4‐thione intermediates followed by coupling with chloroalkyl amines via tandem ring cleavage and C−N/C−S bonds formation enabling the construction of thiazolines/thiazines in one‐pot. This strategy allows broadening the arsenal of synthetic methods to obtain N, S‐heterocycles utilizing substrates prepared according to reported procedures. Abstract :