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

Abstract

1-Substituted 3-alkyl/aryl-3-amino-1 H,3 H-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 α 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-5 H-imidazo[4,5- c]quinoline-2,4-diones. Reaction mechanisms for these transformations are proposed. All compounds were characterized by their 1H, 13C, IR and atmospheric pressure chemical ionization mass spectra and some of them also by 15N NMR data.