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Paper | Special issue | Vol 59, No. 1, 2003, pp.129-136
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S5
A Direct Conversion of 5,6,7,8-Tetrahydro-2H-1-benzopyran-2,5-diones into Substituted 1-Amino-5,6,7,8-tetrahydroquinoline-2,5-diones

Polonca Trebse, Slovenko Polanc, and Marijan Kočevar

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia


A highly selective transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones (1a-c) with hydrazides, arylhydrazines and heterocyclic hydrazines as nitrogen-containing nucleophiles (2) into the corresponding 1-amino-5,6,7,8-tetrahydroquinoline-2,5-diones (5-17) was investi-gated. The reac-tion was carried out in the mixture of ethanol, water and triethylamine, and the corresponding quinoline-2,5-diones were obtained in 52-89% yields. The com-pounds (3) and (4) were proposed to be intermediates in this transformation.