Access to Fully Substituted Thiazoles and 2,3-Dihydrothiazoles via Copper-Catalyzed [4+1] Heterocyclization of alpha-(N-Hydroxy/aryl)imino-beta-oxodithioesters with alpha-Diazocarbonyls

作者：Srivastava Abhijeet; Shukla Gaurav; Yadav Dhananjay; Singh Maya Shankar

来源：Journal of Organic Chemistry, 2017, 82(20): 10846-10854.

DOI：10.1021/acs.joc.7b01601

An efficient chemoselective practical route to fully substituted thiazoles and 2,3-dihydrothiazoles has been devised by [4 + 1] heterocyclization of alpha-(N-hydroxy/aryl)imino-beta-oxodithioesters with in situ generated Cu-carbenoids of diazocarbonyls. The alpha-(N-hydroxy/aryl)imino-beta-oxodithioesters are readily accessible by the reaction of beta-oxodithioesters with nitrous acid/nitrosoarenes. The overall transformation involves sequential N-O/C-N bonds cleavage followed by cascade C-N/C-S bonds formation in one-pot. This new strategy allows full control over the introduction of various sensitive functional groups at different positions of the thiazole ring, broadening the arsenal of synthetic methods to obtain such scaffolds.

• 出版日期2017-10-20