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Synthesis of 2,3-disubstituted 4-oxo-3,4,5,6-tetrahydrospiro-(benzo[h]quinazoline-5,1′-cyclopentanes)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Substituted 4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline-5,1′-cyclopentanes) were obtained by the reaction of 4-amino-3-ethoxycarbonyl-1,2-dihydrospiro(naphthalene-2,1′-cyclopentane) with methyl, phenyl, and benzyl isothiocyanates and cyclization of the obtained thioureas. Condensation of the products with various halides gave 2,3-substituted 4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1′-cyclopentanes). The reaction of 4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline-5,1′-cyclopentane) with 1,2-dibromoethane and 1,3-dibromopropane led to 6-oxo-7,8-dihydrospiro(benzo[h]thiazolidino[2,3-b]quinazoline-7,1′-cyclopentane) and 7-oxo-8,9-dihydrospiro(benzo[h]-perhydrothiazino[2,3-b]quinazoline-8,1′-cyclopentane) respectively.

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References

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A. L. Mndzhoyan Institute of Fine Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Erevan. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 663–667, May, 2000.

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Markosyan, A.I., Kuroyan, R.A. & Dilanyan, S.V. Synthesis of 2,3-disubstituted 4-oxo-3,4,5,6-tetrahydrospiro-(benzo[h]quinazoline-5,1′-cyclopentanes). Chem Heterocycl Compd 36, 579–583 (2000). https://doi.org/10.1007/BF02290849

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  • DOI: https://doi.org/10.1007/BF02290849

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