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

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

 

 

 

Green Chem., 2013, Advance Article
DOI: 10.1039/C3GC37047J, Paper
Maya Shankar Singh, Anugula Nagaraju, Girijesh Kumar Verma, Gaurav Shukla, Rajiv Kumar Verma, Abhijeet Srivastava, Keshav Raghuvanshi
Regioselective synthesis of 1,2,3-thiadiazoles has been achieved via Wolff-type heteroannulation.
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.
http://pubs.rsc.org/en/Content/ArticleLanding/2013/GC/C3GC37047J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29
Maya Shankar Singh ,  Anugula Nagaraju ,  Girijesh Kumar Verma,  Gaurav Shukla ,  Rajiv Kumar Verma ,  Abhijeet Srivastava andKeshav Raghuvanshi
Green Chem., 2013, Advance Article

DOI: 10.1039/C3GC37047J

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