Reaction of 3-aminoquinoline-2,4-diones with isocyanates. Synthesis of novel 3-(3′-alkyl/arylureido)quinoline-2,4-diones and their cyclic carbinolamide isomers

✍ Scribed by Antonín Klásek; Ignác Hoza; Antonín Lyčka; Michal Holčapek

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 138 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430132

✦ Synopsis

Abstract

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3‐Alkyl/aryl‐3‐amino‐1__H__,3__H__‐quinoline‐2,4‐diones react with alkyl/aryl isocyanates to give novel 3‐alkyl/aryl‐3‐ureido‐1__H__,3__H__‐quinoline‐2,4‐diones or 3a‐alkyl/aryl‐9b‐hydroxy‐3,3a,5,9b‐tetrahydro‐1__H__‐imidazo[4,5‐c]quinoline‐2,4‐diones. In some cases, a mixture of both products was obtained and separated by fractional crystallization. All compounds were characterized by their ^1^H, ^13^C, ir and ms data and some of them also by ^15^N nmr data.