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Synthesis, characterization and biological activity of new cyclization products of 3-(4-substituted benzylidene)-2H-pyrido[1,2-a]pyrimidine 2,4-(3H)-diones

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Abstract

A method is presented for the synthesis of 4-(substituted phenyl)-3-(3-substituted phenyl)4H-spiro[isoxazole-5,3′-pyrido[1,2-a]pyrimidine]-2′,4′-dione (3), 3-(4-substituted phenyl)-3H-isoxazole[3, 4-d]pyrido[1,2-a]pyrimidin-4-(3aH)-one (4) and 3-(4-substituted phenyl) 3,3a-dihydropyrazolo[3,4-d]pyrido[1,2-a]pyrimidin-4-(2H)-one (5) which consists of the conversion of 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) to chalcones (2) and their 1,3-dipolar cycloaddition with appropriate aldoximes to give spiro compounds and heterocyclization using amines to yield isoxazolines and pyrazolines. All the compounds were screened for their antimicrobial and antitubercular activity.

1,3-Dipolar cycloaddition of pyrido-pyrimidine chalcones with appropriate aldoximes give spiro compounds; heterocyclization using hydroxylamine or hydrazine to yield isoxazolines or pyrazolines, respectively. All the compounds were then screened for their biological (antimicrobial and antitubercular) activity.

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Acknowledgements

The authors express their sincere thanks to the Head, Department of Chemistry, Lucknow University, Lucknow, for providing laboratory facilities. They are also thankful to the Director, Central Drug Research Institute, Lucknow for elemental analysis, spectral data and biological activity studies.

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Authors and Affiliations

  1. Department of Chemistry, University of Lucknow, University Road, Lucknow, 226 007, India

    ABHA BISHNOI, SURUCHI SINGH & ANIL K TIWARI

  2. Department of Chemistry, Sri Ramswaroop College of Engineering and Management, Faizabad Road, Lucknow, 226 001, India

    KRISHNA SRIVASTAVA

  3. Division of Pharmacology, Central Drug Research Institute, Chattar Manzil Palace, Lucknow, 226 001, India

    RAM RAGHUVIR & CHANDRAKANT M TRIPATHI

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  1. ABHA BISHNOI
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  2. SURUCHI SINGH
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Correspondence to ABHA BISHNOI.

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BISHNOI, A., SINGH, S., TIWARI, A.K. et al. Synthesis, characterization and biological activity of new cyclization products of 3-(4-substituted benzylidene)-2H-pyrido[1,2-a]pyrimidine 2,4-(3H)-diones. J Chem Sci 125, 305–312 (2013). https://doi.org/10.1007/s12039-013-0367-0

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  • DOI: https://doi.org/10.1007/s12039-013-0367-0

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