A facile synthesis and highly atom economic 1,3-dipolar cycloaddition of hexahydropyrido[3,4-c][1,5]benzothiazepines with nitrile oxide: stereoselective formation of hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothiazepines |
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Authors: | Raju Ranjith Kumar |
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Institution: | Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India |
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Abstract: | A series of new 2-methyl-11-aryl-4-(E)-arylmethylidene]-1,2,3,4,11,11a-hexahydropyrido3,4-c]1,5]benzothiazepines were obtained by the reaction of o-aminothiophenol and (E)-1-methyl-3,5-bis(arylidene)-4-piperidones in the presence of a catalytic amount of acetic acid under solvent-free microwave irradiation. These dipolarophiles undergo a highly atom economic 1,3-dipolar cycloaddition with nitrile oxide to afford a series of novel 6-methyl-1-phenyl-8-aryl-4-(E)-arylmethylidene]-4,5,6,7,7a,8-hexahydro1,2,4]oxadiazolo5,4-d]pyrido3,4-c]1,5]benzothiazepines stereoselectively. |
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Keywords: | Benzothiazepine Piperidone 1 3-Dipolar cycloaddition Nitrile oxide |
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