Divergent Synthesis Of Quinoline Derivatives Via [5+1] Annulation Of 2-Isocyanochalcones With Nitroalkanes

Quinoline is an important class of heterocyclic compounds.The antimalarial drugs chloroquine and quinolones both contain quinoline skeleton.The synthetic method of quinoline compounds is particularly important.In this thesis,a simple and effective method for the synthesis of a series of quinoline compounds has been explored by using2-isocyanochalcones,which is easy to prepare,as the raw material.It lays a foundation for the study of its biological activity.This thesis mainly includes the following two parts:in the first part,we summarize the research progress of 2-isocyanochalcones,including its structure characteristics,synthesis,the related reaction and its application.We also generalized the research progress of the quinoline derivatives,structure features and synthetic methods,finally we pointed out the significance of the research.The second part is a development of new DBN-catalyzed[5+1]annulation between2-isocyanochalcones and nitroalkanes.This reaction provides an efficient method for the divergentsynthesisofaromaticquinolines and3-nitrodihydroquinolines.The substrate-dependent controllability on elimination or reservation of the nitro group on the structure of the products is demonstrated in this transformation,which features mild reaction conditions,high efficiency,and readily available substrates.Moreover,the tricyclic pyrrolo[2,3-c]quinolines were constructed from 3-nitrodihydroquinoline through a simple transformation.In this paper,all the products were synthesized by ¹H NMR,¹³CNMR and MS.