A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues

Murru, Siva ; Singh, C.B. ; Kavala, Veerababurao ; Patel, Bhisma K. (2008) A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues Tetrahedron, 64 (8). pp. 1931-1942. ISSN 0040-4020

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Official URL: https://www.sciencedirect.com/science/article/pii/...

Related URL: http://dx.doi.org/10.1016/j.tet.2007.11.076

Abstract

For the first time a reaction intermediate has been isolated giving further insight into the mechanism of thiazol-2-imine formation. The first step of the reaction requires a basic medium, while the second step is an acid mediated E1 elimination reaction. An efficient one-pot synthesis of substituted thiazol-2-imines have been achieved by the condensation of carbonyl compounds with thioureas and 1,3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the p K a s of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of ketones. The methodology is extended to access novel neurodegenerative drug candidate pifithrin-α analogues in good yields in shorter reaction time. This method is simple, versatile and is applicable for different 1,3-disubstituted thioureas as well as a range of carbonyl compounds.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Photochemistry; Reaction Intermediate; One-pot Synthesis; Organic Chemistry; Elimination Reaction; Chemistry; Pifithrin; Thiourea
ID Code:113945
Deposited On:02 May 2018 04:55
Last Modified:02 May 2018 04:55

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