New synthesis on the basis 2‐allyloxy chalcone and NMR studies its some derivatives |
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Authors: | I. G. Mamedov M. R. Bayramov Y. V. Mamedova A. M. Maharramov |
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Affiliation: | Chemical Faculty, NMR Laboratory, Baku State University, Baku, Azerbaijan |
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Abstract: | Synthesis and NMR investigations of cyclohexenone, flavanone, isoxazol and indazole derivatives of (2E)‐3‐[2‐(allyloxy)‐5‐bromophenyl]‐1‐(2‐hydroxy‐5‐methylphenyl)‐2‐propen‐1‐one ( I , chalcone) have been carried out. The results confirm the formation of O–H???O type intramolecular hydrogen bond and intramolecular cyclization in the (2E)‐3‐[2‐(allyloxy)‐5‐bromophenyl]‐1‐(2‐hydroxy‐5‐methylphenyl)‐2‐propen‐1‐one ( I ), the presence of conformational and keto–enol tautomeric transitions in the 6‐acetyl‐5‐[2‐(allyloxy)‐5‐bromophenyl]‐3‐(2‐hydroxy‐5‐methylphenyl)‐2‐cyclohexen‐1‐one ( II ), conformational transitions in the 2‐{4‐[2‐(allyloxy)‐5‐bromophenyl]‐3‐methyl‐4.5‐dihydro‐1.2‐benzisoxazol‐6‐yl}‐4‐methylphenol ( III ) and 2‐{4‐[2‐(allyloxy)‐5‐bromophenyl]‐3‐methyl‐4.5‐dihydro‐1H‐indazol‐6‐yl}‐4‐methylphenol ( IV ). The conformational and keto–enol tautomerism in the investigated compounds have been also confirmed by chemical methods. Copyright © 2014 John Wiley & Sons, Ltd. |
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Keywords: | chalcone flavanone isoxazol indazole cyclohexenone molecular dynamics hydrogen bond keto– enol tautomerism conformational transition NMR spectroscopy |
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