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

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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.

Graphical abstract: Efficient construction of C–N and C–S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate

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Publication details

The article was received on 09 Feb 2017, accepted on 06 Apr 2017 and first published on 06 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00306D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Efficient construction of C–N and C–S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate

    X. Chen, X. Wang, J. Song, Q. Yang, C. Huang and W. Liu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00306D

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