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Efficient One-Pot Synthesis, Structure Elucidation, and Antibacterial Activities of Novel 3-(Adamantan-1-yl)-1-alkyl(aryl, aralkyl, hydroxyethyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazolin-5-ones

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Abstract

A series of novel 3-(adamantan-1-yl)-1-(alkyl, aryl, aralkyl, hydroxyethyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazolin-5-ones have been synthesised by the reaction of 3-(alkyl/aralkyl/aryl)­amino-5,5-dimethylcyclohex-2-en-1-ones with adamantan-1-amine and formaldehyde in refluxing methanol. The initial enaminones were obtained by the condensation of dimedone with primary amines under microwave irradiation. The synthesized compounds were characterized by IR, 1H and 13C NMR, and mass spectra, and X-ray analysis of 3-(adamantan-1-yl)-1-(4-bromophenyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazolin5-one was performed for the final structure assignment. The synthesized compounds were tested for their antibacterial activity.

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Authors and Affiliations

  1. Organic Research Lab., Department of Chemical Science, Assam Don Bosco University, 782402, Sonapur, Assam, India

    S. Kaping, U. Kalita & J. N. Vishwakarma

  2. Division of Animal Health, ICAR Research Complex for North-Eastern Hill Region, 793103, Barapani, Meghalaya, India

    S. Rajkumari & A. Sen

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  1. S. Kaping
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  2. U. Kalita
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  3. S. Rajkumari
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  5. J. N. Vishwakarma
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Correspondence to J. N. Vishwakarma.

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Kaping, S., Kalita, U., Rajkumari, S. et al. Efficient One-Pot Synthesis, Structure Elucidation, and Antibacterial Activities of Novel 3-(Adamantan-1-yl)-1-alkyl(aryl, aralkyl, hydroxyethyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazolin-5-ones. Russ J Org Chem 58, 152–158 (2022). https://doi.org/10.1134/S1070428022010213

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