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Substituted Benzo[ a ]carbazoles and Indoleacetic Acids from Arylglyoxals and Enamines through Domino Condensation, Thermal Cyclization, and Aromatization
Author(s) -
Maity Subhendu,
Pathak Sudipta,
Pramanik Animesh
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402085
Subject(s) - aromatization , chemistry , malononitrile , domino , condensation , cyclohexanone , hydrolysis , organic chemistry , medicinal chemistry , catalysis , physics , thermodynamics
A two‐step method has been developed in which cyclohexanone‐fused 2‐(3‐pyrrolyl)‐2‐cyanoacetamides, the condensation products of enamines, arylglyoxals, and malononitrile, are converted into highly substituted benzo[ a ]carbazoles through a one‐step thermal cyclization and palladium‐catalyzed aromatization. The biologically important indoleacetic acid derivatives are also obtained in good yields from the hydrolysis and aromatization of the same cyanoacetamides.