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Catalyst-free multicomponent synthesis of novel adamantyl-containing tetrahydropyrimidine carboxylates

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Abstract

\(\beta \)-Enaminoesters were generated in situ by the reaction of aliphatic or aromatic primary amines to electron-deficient alkynes, dimethyl acetylenedicarboxylate, and methyl propiolate. \(\beta \)-Enaminoesters thus formed were reacted with 1-adamantanamine and formaldehyde in methanol to give novel molecular hybrids: dimethyl 3-((3s,5s,7s)-adamantan-1-yl)-1-(alkyl/aralkyl/aryl)-1,2,3,4-tetrahydropyrimidine-5,6-dicarboxylates (5a–j) and methyl 3-((3s,5s,7s)-adamantan-1-yl)-1-(alkyl/aralkyl/aryl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates (9a–j). The structures of the molecular hybrids have been established based on the spectral and analytical data. Structural confirmation of the products was done by X-ray crystallography of 5d as a representative product of the series.

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Acknowledgments

Authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. Authors also wish to express their gratitude to IIT, Guwahati, Tezpur University, Tezpur, SAIF–NEHU, Shillong and SAIF–CDRI, Lucknow for providing spectral and analytical data. Our thanks are also due to the Department of Biotechnology (DBT), Government of India for a research. UK and SK thanks DBT–GOI for research fellowships.

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  1. Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Airport Road, Azara, Guwahati, 781017, India

    Utpalparna Kalita, Shunan Kaping & Jai Narain Vishwakarma

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  1. Utpalparna Kalita
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  2. Shunan Kaping
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  3. Jai Narain Vishwakarma
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Correspondence to Jai Narain Vishwakarma.

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Kalita, U., Kaping, S. & Vishwakarma, J.N. Catalyst-free multicomponent synthesis of novel adamantyl-containing tetrahydropyrimidine carboxylates. Mol Divers 20, 581–590 (2016). https://doi.org/10.1007/s11030-015-9653-8

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