Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

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

Access to Fully Substituted Thiazoles and 2,3-Dihydrothiazoles via Copper-Catalyzed [4 + 1] Heterocyclization of α-(N-Hydroxy/aryl)imino-β-oxodithioesters with α-Diazocarbonyls
Abhijeet Srivastava, Dhananjay Yadav, Maya Shankar Singh, Gaurav Shukla
An efficient chemoselective practical route to fully substituted thiazoles and 2,3-dihydrothiazoles has been devised by [4 + 1] heterocyclization of α-(N-hydroxy/aryl)imino-β-oxodithioesters with in situ generated Cu-carbenoids of diazocarbonyls. The α-(N-hydroxy/aryl)imino-β-oxodithioesters are readily accessible by the reaction of β-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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01601

DOI: 10.1021/acs.joc.7b01601

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