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

Smith, Keith, El-Hiti, Gamal A., Abdo, Mohamed A. and Abdel-Megeed, Mohamed F. 1995. Regiospecific electrophilic substitution of aminoquinazolinones: directed lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methylquinazolin-4(3H)-ones. Journal of the Chemical Society, Perkin Transactions 1 (8) , pp. 1029-1033. 10.1039/P19950001029

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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.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:51
URI: http://orca-mwe.cf.ac.uk/id/eprint/12689

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