Abstract
The reaction of cyclohexanone with arylidenebisureas (e.g. benzal-bisurea) in an acid medium has given 4, 4′-diaryl-2, 2′-dioxo-5, 5′-trimethylene-6, 6′-spirobishexahydropyrimidines (II). The acid hydrolysis of IIa (aryl-C6H5) in the presence of 2, 4-dinitrophenylhydrazine leads to the 2, 4-dinitrophenylhydrazone of 2-hydroxy-8-oxo-4-phenyl-5, 6, 7, 8-tetrahydroquinazoline (IV). Compound IV was also obtained by the ozonization of 2-acetoxy-8-benzal-4-phenyl-5, 6, 7, 8-tetrahydroquinazoline (IX) and subsequent decomposition of the ozonide with a solution of 2, 4-dinitrophenylhydrazine. The structure of the compounds obtained was confirmed by means of their IR, UV, and PMR spectra. Corresponding 6, 6′-spirobishexahydropyrimidines have also been obtained from 2-methylcyclohexanone, acetone, and methyl ethyl ketone and benzalbisurea.
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For part XIV, see [1].
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Sedova, V.F., Mamaev, V.M. Pyrimidines. Chem Heterocycl Compd 4, 667–671 (1971). https://doi.org/10.1007/BF00481053
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DOI: https://doi.org/10.1007/BF00481053