Russian Journal of Organic Chemistry

, Volume 39, Issue 3, pp 430–435 | Cite as

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

  • K. Smith
  • G. A. El-Hiti
  • M. F. Abdel-Megeed
Article

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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Copyright information

© MAIK “Nauka/Interperiodica” 2003

Authors and Affiliations

  • K. Smith
    • 1
  • G. A. El-Hiti
    • 1
  • M. F. Abdel-Megeed
    • 2
  1. 1.Center for Clean Chemistry, Department of ChemistryUniversity of WalesSwanseaUK
  2. 2.Department of Chemistry, Faculty of ScienceTanta UniversityTantaEgypt

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