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Molecular rearrangement of 1-substituted 3-aminoquinoline-2,4-diones in their reaction with urea and nitrourea synthesis and transformations of reaction intermediates

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

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
523 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Substituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones (6) react with nitrourea to give 3-ureido-1H,3H-quinoline-2,4-diones (10), 9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones (11), and 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones (12). Compounds 11 were dehydrated to 12 by the action of phosphorus pentoxide. All three types of compounds rearrange in boiling acetic acid to give three different types of products of molecular rearrangement. A proposed reaction mechanism is discussed.

📜 SIMILAR VOLUMES

Reaction of 3-aminoquinoline-2,4-diones
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
✍ Antonín Klásek; Ignác Hoza; Antonín Lyčka; Michal Holčapek 📂 Article 📅 2006 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 138 KB

## Abstract magnified image 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