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K2CO3 catalyzed regioselective synthesis of thieno[2,3-b]thiochromen-4-one oximes: access to the corresponding amine and nitroso derivatives

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Abstract

An unprecedented and efficient method for the synthesis of useful thieno[2,3-b]thiochromen-4-one oximes is accomplished via a thio[3 + 2] cyclization reaction of 4-hydroxydithiocoumarins and trans-β-nitrostyrenes in the presence of 10 mol% K2CO3 in ethanol under reflux conditions. Furthermore, hitherto, these precursors were converted into the corresponding 2-amino thieno[2,3-b]thiochromen-4-one and 2-nitroso thieno[2,3-b]thiochromen-4-one derivatives respectively. The salient features of the present protocol are mild reaction conditions, shorter reaction times, good yields and unexpected formation of C–C and C–S bonds in a regioselective manner.

Graphical abstract: K2CO3 catalyzed regioselective synthesis of thieno[2,3-b]thiochromen-4-one oximes: access to the corresponding amine and nitroso derivatives

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Publication details

The article was received on 28 Apr 2017, accepted on 13 Jun 2017 and first published on 13 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01033H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    K2CO3 catalyzed regioselective synthesis of thieno[2,3-b]thiochromen-4-one oximes: access to the corresponding amine and nitroso derivatives

    K. Mahato, P. R. Bagdi and A. T. Khan, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01033H

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