Thiourea to bicyclic scaffolds: highly regio- and stereoselective routes to dithiazolopyrimidines |
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| Authors: | Lal Dhar S. Yadav Vijai K. Rai |
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| Affiliation: | Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, Uttar Pradesh, India |
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| Abstract: | Microwave-activated solvent-free Michael addition of 3-imino-1,4,2-dithiazoles to 4-arylidene-5(4H)-oxazolones furnished isolable adducts regio- and diastereoselectively, which underwent ring transformation to yield the target dithiazolopyrimidines. Alternatively, the similar conjugate addition of methanesulfinylmethylisothioureas to 4-arylidene-5(4H)-oxazolones diastereoselectively afforded Michael adducts, which underwent ring transformation followed by heterocyclization via deoxygenative demethylation with thionyl chloride to yield the same products dithiazolopyrimidines regio- and diastereoselectively. |
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| Keywords: | Microwaves Thiourea Diastereoselective synthesis Dithiazolopyrimidines Michael addition |
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