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Synthesis 1995; 1995(3): 251-252
DOI: 10.1055/s-1995-3894
short paper
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Macrocyclic Analogues of Barbituric Acid by Ring Enlargements of Macrocyclic Imides

Thomas Koch, Manfred Hesse*
  • *Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland, Fax + 41(1)361+9895
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Publication History

Publication Date:
31 December 2000 (online)

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The 14-membered imide 1 reacts with different isocyanates to the [n+2]-Zip ring-enlargement products 2a-d in high yields. These 16-membered heterocycles can be regarded as macrocyclic analogues of barbituric acid. Using the more reactive phenyl isocyanate the twofold ring-enlarged 18-membered compound 5 was formed.

Macrocyclic imides react under ring enlargement with isocyanates.