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Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives

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Abstract

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.

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Authors and Affiliations

  1. Center for Clean Chemistry, Department of Chemistry, University of Wales, Swansea, SA2 8PP, UK

    K. Smith & G. A. El-Hiti

  2. Department of Chemistry, Faculty of Science, Tanta University, Tanta, 31527, Egypt

    M. F. Abdel-Megeed

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  1. K. Smith
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  2. G. A. El-Hiti
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  3. M. F. Abdel-Megeed
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Smith, K., El-Hiti, G.A. & Abdel-Megeed, M.F. Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives. Russian Journal of Organic Chemistry 39, 430–435 (2003). https://doi.org/10.1023/A:1025558201900

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