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Issue 4, 2013
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Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via[3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions

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Abstract

An efficient, sustainable, and regioselective one-pot synthesis of hitherto unreported 4-aroyl/hetaroyl/alkanoyl-5-alkyl/allyl/benzylsulfanyl-1,2,3-thiadiazoles has been achieved by [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide through cascade 1–2 (S–N) and 3–4 (C–N) bond connections involving Wolff-type heterocyclization. Optimally, the reactions are very fast and completed within 2–15 minutes, when a mixture of α-enolicdithioester and tosyl azide was stirred at 0 °C in the presence of Et3N under solvent-free conditions. Furthermore, no co-catalyst or activator is necessary. The eco-compatibility, mild conditions, excellent yields, easy purification, and avoidance of expensive/toxic reagents are advantages of this protocol to access this medicinally privileged substructure.

Graphical abstract: Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions

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Supplementary files

Article information


Submitted
17 Dec 2012
Accepted
28 Jan 2013
First published
28 Jan 2013

Green Chem., 2013,15, 954-962
Article type
Paper

Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions

M. S. Singh, A. Nagaraju, G. K. Verma, G. Shukla, R. K. Verma, A. Srivastava and K. Raghuvanshi, Green Chem., 2013, 15, 954
DOI: 10.1039/C3GC37047J

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