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Chen XB, Wang XQ, Song JN, et al. Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Org Biomol Chem. 2017;15(17):3611-3615doi: 10.1039/c7ob00306d.
Chen, X. B., Wang, X. Q., Song, J. N., Yang, Q. L., Huang, C., & Liu, W. (2017). Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Organic & biomolecular chemistry, 15(17), 3611-3615. https://doi.org/10.1039/c7ob00306d
Chen, Xue-Bing, et al. "Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate." Organic & biomolecular chemistry vol. 15,17 (2017): 3611-3615. doi: https://doi.org/10.1039/c7ob00306d
Chen XB, Wang XQ, Song JN, Yang QL, Huang C, Liu W. Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Org Biomol Chem. 2017 May 03;15(17):3611-3615. doi: 10.1039/c7ob00306d. PMID: 28401235.
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Org Biomol Chem. 2017 May 03;15(17):3611-3615. doi: 10.1039/c7ob00306d.

Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate.

Organic & biomolecular chemistry

Xue-Bing Chen, Xue-Quan Wang, Jia-Na Song, Qing-Li Yang, Chao Huang, Wei Liu

Affiliations

  1. Key Laboratory of Natural Pharmaceutical and Chemical Biology of Yunnan Province, School of Science Honghe, University Mengzi, Yunnan 661100, China. [email protected].

PMID: 28401235 DOI: 10.1039/c7ob00306d

Abstract

A novel and highly efficient protocol has been developed for the regioselective synthesis of 2-iminothiazole derivatives with potential biochemical interest by the reaction of enaminones, potassium thiocyanate (KSCN), and N-bromo succinimide (NBS) under mild conditions. The reaction proceeds via the formation of α-bromo enaminones as a versatile intermediate followed by thiocyanation/intramolecular cyclization in a one pot manner. The developed method is particularly attractive due to various advantages including operational simplicity, mild conditions, being catalyst free, and high bond-forming efficiency. The proposed protocol explores the synthetic routes of thiazoles by using various functional enaminones.

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