Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.
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.
Zhang
Xiaoxiang
X
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.
Teo
Wan Teng
WT
Sally
Chan
Philip Wai Hong
PW
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
D000480:Alkynes; D020005:Propanols; D013844:Thiazoles; D013854:Thioamides; D014050:Toluene; C028255:propargyl alcohol; C065428:4-toluenesulfinic acid