H. Choi, D. Chi
May 31, 2004
Citations
1
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract 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 ).