Study On The Synthesis Of3-Aminoquinolines

Aminoquinoline (Aminoquinoline, AQ) as an important class of quinoline derivatives,compared to other quinoline derivatives having high biological activity, has been widelyused in drug screening and modification. AQ and its derivatives present not only in a largenumber of anti-malarial, anti-hypertensive drugs and antibiotics occupies a very importantposition, but also because of its well-coordinated metal ions and relatively high selectivityin chemical analysis has also been a growing body of research and applications.Meanwhile, AQ biological macromolecules such as DNA embedded in the body, such asfluorescent probes in molecular biology has also been widely used.。This paper describes the synthesis of3-amino-described quinoline derivative. On thebasis of a large number of past literature review on the nature of this paper, syntheticmethods quinoline and its derivatives research progress and application of elaborate, andthrough the methods reported in the literature to optimize and improve the successfuldesign and synthesis of8-nitro-3-AQ,7-nitro-3-AQ,6-nitro-3-AQ,5-nitro-3-AQ,8-methoxy3-AQ,7-methoxy-3-AQ,6-methoxy-3-AQ,5-methoxy-3-AQ,8-chloro-3-AQ,7-chloro-3-AQ,6-chloro-3-AQ,5-chloro-3-AQ,12kinds of3-AQ derivatives as the study of new drugintermediates.In this experiment we tried three different routes to synthesis of3-AQ:Doebner-Miller cyclization; Bromide and ammoniated by Buchwald–Hartwig; Friedl ndercyclization.Doebner-Miller cyclization, through aromatic amino compound and ethoxycarbonylmethylene cyclization, dehydrogenation dechlorination, hydrolysis, Curtius rearrangement,raw materials readily available every step of the high yield, but the lengthy route, the routefor its useful intermediates have reference.Bromide by the quinoline compounds in Buchwald-Hartwig reaction, the yield isgood, the route is simple, but in the selective bromination of an electron donatinggroup-containing quinoline ring good. In response to this shortcoming we designed a thirdroute through amino and nitro benzaldehyde dimethyl acetal Friedl nder cyclization nitroquinoline then to give the target compound, simple steps to good yields.