450409-58-2Relevant academic research and scientific papers
Simple preparation of 7-alkylamino-2-methylquinoline-5,8-diones: Regiochemistry in nucleophilic substitution reactions of the 6- or 7-bromo-2-methylquinoline-5,8-dione with amines
Choi, Han Young,Chi, Dae Yoon
, p. 4945 - 4951 (2004)
7-Alkylamino-2-methylquinoline-5,8-diones (7) were prepared from 6-bromo-2-methylquinoline-5,8-dione (2) not from 7-bromo-2-methylquinoline-5,8- dione (1). The chemistry of the transformation of 6-bromo-2-methylquinoline-5,8- dione (2) and various alkylamines, such as piperidine, 2-methylaziridine, benzylamine, n-butylamine, cyclohexylamine, t-butylamine, and ammonia, to 7-alkylamino compounds 7 as well as the transformation of 7-bromo compound 1 and the alkylamines to 6-alkylamino-2-methylquinoline-5,8-diones 11 was studied. The efficient and simple synthetic routes of the key intermediates, 6- and 7-bromo-2-methylquinoline-5,8-diones (2 and 1), from 5,8-dihydroxy-2- methylquinoline (15) and 5,7-dibromo-8-hydroxy-2-methylquinoline (9), respectively, were developed. We also proposed the mechanism for the unusual regioselectivity on the nucleophilic amination of 6- and 7-bromo-2- methylquinoline-5,8-diones (2 and 1).
Preparation of 7-alkylamino-2-methylquinoline-5,8-diones
Choi, Han Young,Kim, Dong Wook,Chi, Dae Yoon,Yoon, Eun Young,Kim, Dong Jin
, p. 5390 - 5393 (2007/10/03)
Several novel 7-alkylamino-2-methylquinoline-5,8-diones (2) were synthesized from 2,5-dimethoxyaniline in five steps via the Skraup reaction followed by demethylations, oxidative bromination, amination, and debromination. We have achieved an unusual hydrobromic acid catalyzed debromination reactions of several 6-bromo-7-alkylamino-2-methylquinoline-5,8-diones, giving 7-alkylamino-2-methylquinoline-5,8-diones in good yields.
