title: Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.
abstract: A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·H(2)O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.
authors.forename: Xiaoxiang
authors.initials: X
authors.lastname: Zhang
authors.forename: Wan Teng
authors.initials: WT
authors.lastname: Teo
authors.lastname: Sally
authors.forename: Philip Wai Hong
authors.initials: PW
authors.lastname: Chan
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000480:Alkynes; D020005:Propanols; D013844:Thiazoles; D013854:Thioamides; D014050:Toluene; C028255:propargyl alcohol; C065428:4-toluenesulfinic acid