Structural Chemistry

, Volume 5, Issue 6, pp 375–381 | Cite as

Ring closure of diethyl 2-methoxy-2-[N-(5-amino-1-benzylimidazolyl-4-carbonyl)amino]malonate: Product structures and pathways of product formation

  • Anila Bhan
  • Ramachandra S. Hosmane
  • Hongming Zhang
  • Narayan S. Hosmane


Ring closure of the title compound (1) with sodium methoxide in methanol yielded three products, one 5∶6-fused and two 5∶7-fused heterocyclic systems: 9-benzyl-2-methoxycarbonylhypoxanthine (2), 3-benzyl-4,5,7,8-tetrahydro-6-methoxy-6-methoxycarbonyl-6H-imidazo[4,5-e][1,4]-diazepine-5,8-dione (3), and 3-benzyl-4,5,7,8-tetrahydro-6-methoxy-6H-imidazo[4,5-e][1,4]-diazepine-5,8-dione (4). Structures and pathways of formation of all three products have been described. Structures of2 and3 were confirmed by single-crystal X-ray diffraction analyses.

Key words

Imidazoles purines imidazol[4,5-e][1,4]diazepines X-ray crystallography 


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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • Anila Bhan
    • 2
  • Ramachandra S. Hosmane
    • 2
  • Hongming Zhang
    • 1
  • Narayan S. Hosmane
    • 1
  1. 1.Department of ChemistrySouthern Methodist UniversityDallas
  2. 2.Laboratory for Drug Design and Synthesis, Department of Chemistry and BiochemistryUniversity of Maryland Baltimore CountyBaltimore

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