Diversity oriented synthesis of fused-ring 1,3-oxazines from carbohydrates as biorenewable feedstocks |
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Authors: | Lal Dhar S Yadav Vishnu P Srivastava Vijai K Rai Rajesh Patel |
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Institution: | Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India |
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Abstract: | Microwave enhanced diversity oriented synthesis (MEDOS) of various N- and O-heterocyclic systems fused with 1,3-oxazine ring is reported. The synthesis represents a new montmorillonite K-10 clay-catalyzed green protocol, which utilizes d-glucose/d-xylose as biorenewable feedstocks. d-Glucose/d-xylose-derived 1,3-oxazin-2-ones(thiones) either directly undergo K-10 clay-catalyzed cyclization to yield pyrano-/furo-1,3-oxazine systems under solvent-free microwave irradiation conditions or afford azolo-/azino-1,3-oxazines when subjected to Malaprade reaction followed by cyclization with appropriate reagents, viz. phenylhydrazine, hydroxylamine, acetamidine, phenylurea and semi(thiosemi)carbazide. |
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Keywords: | Diversity oriented synthesis 1 3-Oxazines Solvent-free Microwaves Montmorillonite K-10 Carbohydrates |
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