Reaction of 1-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones with urea. Synthetic route to novel 3-(3-acylureido)-2,3-dihydro-1H-indol-2-ones, 4-alkylidene-1 ' H-spiro[imidazolidine-5,3 '-indole]-2,2 '-diones, and 3,3a-dihydro-5H-imidazo [4,5-c] quino

摘要

1-Substituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with urea in boiling acetic acid to give products depending on the type of substitution in position 3 and at the nitrogen atom of the 3-amino group. Starting compounds bearing a primary amino group in position 3 give 3-(3-acylureido)-2,3-dihydro-1'H-indol-2-ones. Starting compounds bearing a secondary amino group in position 3 react according to the character of the other substituent in position 3. If there is a hydrogen atom a to the carbon atom C(3), 4-alkylidene-1'H-spiro[imidazolidine-5,3'-indole]-2,2'-diones arise. If a hydrogen atom is not present in this position, the reaction leads to 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones. Reaction mechanisms for these transformations are proposed. All compounds were characterized by their H-1, C-13, IR and atmospheric pressure chemical ionization mass spectra and some of them also by N-15 NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved. [References: 8]