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Issue 8, 1995
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Regiospecific electrophilic substitution of aminoquinazolinones: directed lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methylquinazolin-4(3H)-ones

Abstract

The 2-methyl group in 3-(pivaloylamino)- and in 3-(acetylamino)-2-methyIquinazolin-4(3H)-ones has been lithiated with butyllithium. The lithium reagents thus obtained react with a variety of electrophiles (benzophenone, methyl iodide, D2O, cyclohexanone, acetophenone, phenyl isocyanate) to give the corresponding substituted derivatives in very good yields. The amide group has been cleaved in good yield under basic conditions for one model case to provide convenient access to 3-amino-2-ethylquinazolin-4(3H)- one. The NMR spectra of the 2-substituted 3-acylaminoquinazolin-4(3H)-ones show diastereotopism of the CH2 group at position 2.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1995, 1029-1033
Article type
Paper

Regiospecific electrophilic substitution of aminoquinazolinones: directed lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methylquinazolin-4(3H)-ones

K. Smith, G. A. El-Hiti, M. A. Abdo and M. F. Abdel-Megeed, J. Chem. Soc., Perkin Trans. 1, 1995, 1029
DOI: 10.1039/P19950001029

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