Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives |
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| Authors: | Smith K El-Hiti G A Abdel-Megeed M F |
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| Institution: | (1) Center for Clean Chemistry, Department of Chemistry, University of Wales, Swansea, SA2 8PP, UK;(2) Department of Chemistry, Faculty of Science, Tanta University, Tanta, 31527, Egypt |
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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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