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Synthesis and antimicrobial evaluation of novel polyheterocyclic ring systems derived from 2-oxo-2H-pyrimido[2,1-b]benzothiazole-3-carbonitrile

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Abstract

New functionalized triheterocyclic ring systems, pyrazolo[4′,3′:5,6]pyrimido[2,1-b]benzothiazol-4(1H)-ones 4a, b, pyrano[3′,4′:5,6]pyrimido[2,1-b][1,3]benzothiazol-5-one 6, and pyrido[3′,4′:5,6]pyrimido[2,1-b][1,3]benzothiazoles 8,9 were efficiently synthesized via the reaction of 2-oxo-2H-pyrimido[2,1-b]benzothiazole-3-carbonitrile (3) with hydrazines, acetylacetone, malononitrile, and cyanoacetamide, respectively. Hydrolysis of 3 with PPA afforded 2-oxo-2H-pyrimido[2,1-b]benzothiazole-3-carboxamide (10). The reactions of 3 with a variety of α-aminoazoles afforded the tetra- and penta-heterocyclic ring systems 11–14. The mechanism and the regioselectively of the studied reactions have been discussed. The prepared compounds were screened for their antimicrobial activity against a panel of bacteria and fungi strains and some derivatives showed promising antimicrobial activity.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, King Khalid University, Abha, 9004, Saudi Arabia

    Samir Bondock

  2. Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt

    Samir Bondock

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  1. Samir Bondock
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Correspondence to Samir Bondock.

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Bondock, S. Synthesis and antimicrobial evaluation of novel polyheterocyclic ring systems derived from 2-oxo-2H-pyrimido[2,1-b]benzothiazole-3-carbonitrile. Res Chem Intermed 41, 5451–5462 (2015). https://doi.org/10.1007/s11164-014-1672-z

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  • DOI: https://doi.org/10.1007/s11164-014-1672-z

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