Journal of Organic Chemistry p. 4927 - 4931 (1981)
Update date:2022-08-03
Topics:
Bobowski, George
Morrison, Glenn C.
The treatment of 2-<<2-(1H-indol-3-yl)ethyl>imino>cyclohexanone (1) with hot concentrated sulfuric acid to give the pentacyclic compound 4 is described.The treatment of 4 with 2 equiv of isocyanate gave N,3-disubstituted 3,3a,4,4a,10,10a-hexahydro-3a-hydroxy-2-oxo-1,9b:4,10-diethanoimidazo<4,5-b>carbazole-5(2H)-carboxamides 11.When bulky isocyanates were used, the reaction stopped at the diurea stage 10.The latter were irreversibly converted to 11 by heating at 140 deg C.
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