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Synthesis 1996; 1996(8): 959-962
DOI: 10.1055/s-1996-4326
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Reactions of Heterocyclic Ketene Aminals with Dimethyl Oxalate: A Facile Synthesis of γ-Lactam Fused 1,3-Diazaheterocycles

Chu-Yu Yu, Li-Ben Wang, Wen-Yi Li, Zhi-Tang Huang*
  • *Institute of Chemistry, Academia Sinica, Beijing 100080, People’s Republic of China, Fax +86(1)2569564
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Publication Date:
31 December 2000 (online)

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Heterocyclic ketene aminals 1 or 2 react with dimethyl oxalate at room temperature in the presence of sodium hydride to produce the γ-lactam fused 1,3-diazaheterocycles, 7-aroyl-2,3-dihydro-6-hydroxy-5H-pyrrolo[1,2-a]imidazol-5-ones 3 or 8-aroyl-2,3,4,5-tetrahydro-7-hydroxy-6H-pyrrolo[1,2-a]pyrimidin-6-ones 4, respectively, in good yields. A reasonable mechanism which involves N-acylation and intramolecular condensation steps was proposed. Under similar conditions, 1 and ethyl formate reacted to form only the N-formylation products, 2-(aroylmethylene)-1-formylimidazolidines 5, in high yields.

heterocyclic ketene aminals - dimethyl oxalate - ethyl formate - γ-lactam fused 1,3-diazaheterocycles - N-formylation

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