An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization |
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Authors: | Gundibasappa K. Nagaraja Vijayavittala P. Vaidya Koodamara Sheshappa Rai Kittappa M. Mahadevan |
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Affiliation: | 1. Department of PG Studies and Research in Polymer Science , University of Mysore, Sir M. V. PG Centre, Thubinakere , Mandya , Karnataka , India;2. Department of PG Studies and Research in Chemistry , Kuvempu University, Shankaraghatta , Shimoga , Karnataka , India |
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Abstract: | A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a–f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a–f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a–f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, 1H and 13C NMR, and mass spectral data. |
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Keywords: | 1-amino-2-mercapto-5-aryl-1,3,4-triazole chalcones heterocycliczation microwave irradiation o-phenylenediamine |
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