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Synthesis 1994; 1994(12): 1441-1444
DOI: 10.1055/s-1994-25710
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The Regiospecific N-Alkylation of Heterocyclic Ketene Aminals with Ethyl Bromoacetate: A Facile Route to 3-Pyrrolidinone Fused Diazaheterocycles

Li-Ben Wang* , Chu-Yi Yu, Zhi-Tang Huang
  • *Institute of Chemistry, Academia Sinica, Beijing, 100080, People's Republic of China
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Publication Date:
25 April 2002 (online)

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Heterocyclic ketene aminals 1 or 2 react with ethyl bromoacetate in the presence of sodium hydride to afford the N-alkylation products, ethyl [2-(aroylmethylene)imidazolidin-1-yl]acetates 3 or ethyl [2-(aroylmethylene)hexahydropyrimidin-1-yl]acetates 4. Compound 4 could be easily transformed into fused heterocycles 5 by a further cyclocondensation reaction.