Study On Synthesis Of Novel Heterocycle-fused Coumarins And Thienopyridines

With the development of organic synthesis technology and the deep research of coumarin chemistry,coumarins and thienopyridines have been paid more and more attention because of its great application value in the fields of medicine,fragrance,dye,analysis and pesticide.In this paper,coumarins and thienopyridines as the substrate for the reaction of heterocyclic modified coumarins and thienopyridines synthesis method to explore.The paper is divided into three parts.In the first part,4-aminocoumarin was used as the starting material to study the synthesis of new of novel isocoumarino[3',4':4,5]pyrrolo[3,2-c]coumarines by Domino reaction with ninhydrin under p-toluenesulfonic acid as catalyst.In the second part,2-amino-1,4-naphthoquinone was used as the starting material to study the synthesis of novel benz [f] indolo [3,2-c]-isochromeno-5,7,13-triones by Domino reaction with ninhydrin in the presence of p-toluenesulfonic acid with good yields.The third part,an efficient method for the preparation of thieno[3',2':2,3] pyrido [4,5-d] thiazolo [3,2-a] pyrimidin-5-ones is described.The key intermediate,7-(3-amino-4-cyano-5-phenyl aminothieno-2-yl)-5 H-thiazolo [3,2-a] pyrimidin-5-one,was synthesized from 7-chloromethyl-5 H-thiazolo [3,2-a] pyrimidin-5-one with potassium-(2,2-dicyano-1-phenylaminoethen-1-yl)thiolate by Thorpe-Ziegler isomerization.Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet-Spengler reaction provided thieno-pyridine fused thiazolo[3,2-a]pyrimidines under p-toluenesulfonic acid as catalyst in goodyields.The structures of the synthesized compounds were characterized by IR,1HNMR,elemental analysis and so on.