Sevil Özcan, Sevil Özcan, M. Balci
Jun 2, 2008
Citations
0
Influential Citations
37
Citations
Journal
Tetrahedron
Abstract
Abstract Homophthalic acid was reacted with thionylchloride/DMF and chloroethylformate/NEt 3 in the presence and absence of NaN 3 . In all cases completely different isocoumarin derivatives were obtained. These unusual isocoumarin derivatives were isolated and characterized and their formation mechanisms are discussed. The homophthalic acid monomethyl ester was converted into the corresponding isocyanate. Reaction of the isocyanate with different amines produced the urea derivatives. Base-supported condensation reactions of these products gave first an indolinone derivative, which underwent further intermolecular condensation to give substituted indole derivatives. However, when the condensation reaction was carried out in the presence of acetic anhydride, the intermolecular reactions were suppressed. This methodology opens up a new way of synthesizing of various five-membered ring substituted indole derivatives.