One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides

Abstract

A convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine hydrolysis and oxidation protocols.

Catalytic Regio‐ and Stereoselective Alkene Sulfenoamination for 1,4‐Benzothiazine Synthesis

“…For the styrene‐derived substrates, the nitrogen was uniformly added to the benzylic position, whereas the sulfur was attached to the homobenzylic carbon. This regiochemical outcome was distinct from our previously developed alkene sulfenoamination based on halogenation protocols, in which the more nucleophilic sulfur was usually added to the benzylic position . For aliphatic alkenes, the regioselectivity was lower and favored the addition of the nitrogen atom to the terminal position, while the sulfur atom was attached to the internal position.…”

Modular synthesis of thiazoline and thiazole derivatives by using a cascade protocol

“…Thiazoline derivative has also been oxidized with DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) to form thiazoles (entry C). 9 In a continuation of our efforts to get novel small molecule heterocycles 10 , 11 by using domino protocol, 12 we report the synthesis of thiazoline and thiazole derivatives using a domino protocol, mild reaction conditions, and readily available substrates ( Scheme 1 ).…”

Hypervalent iodine-catalyzed conjugate addition with sulfonamides

“…[33][34][35] Given these features, we wondered if the practical features of hypervalent iodine catalyst could be suited for the development of an efficient aza-Michael reaction. As part of our research interest in synthetic methods design to access useful nitrogen-containing compounds, [36][37][38][39][40][41][42][43][44] we disclose here a practical hypervalent iodine-catalyzed aza-Michael reaction with simple sulphonamides as the nitrogen nucleophile (Scheme 1c).…”