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Unexpected products from carbonylation of lithiated quinazolin-4(3H)-one derivatives

Smith, Keith, El-Hiti, Gamal and Abdel-Megeed, M. F. 2003. Unexpected products from carbonylation of lithiated quinazolin-4(3H)-one derivatives. Russian Journal of Organic Chemistry = Zhurnal Organicheskoi Khimii 39 (3) , pp. 430-435. 10.1023/A:1025558201900

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Doubly lithiated 3-pivaloylaminoquinazolin-4(3H)-one reacts with carbon(II) oxide at 0°C to give 77% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetylaminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)-one. Carbonylation of doubly lithiated 2-alkyl-3-aminoquinazolin-4(3H)-ones at 0°C results in deamination to give 2-alkylquinazolin-4(3H)-ones in good yields.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Springer Verlag
ISSN: 1070-4280
Last Modified: 04 Jun 2017 02:51

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