TsNBr 2 promoted cascade formation of C–N and C–S bond: Metal-free synthesis of 2-aminothiazoles from ketones or ketoximes using thiourea
Tetrahedron, ISSN: 0040-4020, Vol: 149, Page: 133721
2023
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Article Description
An efficient metal-free protocol for the synthesis of 2-aminothiazole via the C–N/C–S bond-forming reaction has been developed by treating ketones and thiourea with TsNBr 2. The cascade reaction proceeds via the isolable α-bromoketone and α,α-dibromoketone intermediates in methanol at reflux temperature. Both aromatic and aliphatic ketones undergo oxidative cyclization with thiourea to give the desired product in high yield within a short reaction time. Additionally, we have also developed another strategy for the synthesis of 2-aminothiazole from ketoximes under the same optimized conditions using TsNBr 2 and thiourea.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040402023005239; http://dx.doi.org/10.1016/j.tet.2023.133721; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85176248275&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040402023005239; https://dx.doi.org/10.1016/j.tet.2023.133721
Elsevier BV
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