Synthesis Of Pyran Derivatives Under Solvent-free Conditions

The multicomponent reaction under solvent-free condition is widely used in the synthesis of organic synthesis,which has the advantages of no use of solvents,saving resources,high synthesis efficiency,simple operation,environment friendliness,high atomic economy,and so on.Amino-benzochromenes is the basic component of some natural compounds and has a wide range of biological and pharmacological activities,such as anti platelet aggregation activity,antifungal activity,resistance to cytotoxic activity,which is available as an insecticide,antibacterial agent,analgesic,antipyretic,antihistamines,and drugs for proliferative diseases treatment.Therefore,study on synthesis of pyran derivatives under solvent free condition has important significance.The synthesis of amino-benzochromenes derivatives under solvent-free conditions have been studied.The main research content is as follows:We have synthesized 2-amino-3-cyano-1,4,5,6-4H-pyrano[3,2-c]quinoline-5-ketone derivatives by three-component condensation of aldehyde,malononitrile and 4-hydroxyl-quinoline-2-ketone under solvent free condition at 80 ℃ using ionic liquid propionic ethanolamine(2-HEAP)as catalyst respectively with 86%-94% yield in 2min-20 min.The recovered catalyst can be reused at least four additional times in subsequent reactions without considerable decrease in catalytic activity.We have synthesized 2-phenylsulfonyl-3-amino-4H-naphthopyran derivatives by threecomponent condensation of aldehyde,benzene sulfonyl acetonitrile and 2-naphthol under solvent free condition at 110℃ using potassium phthalimide(PPI)and K3PO4.3H2 O as catalyst with good yield between 66%-92% in 2min-35 min.The catalyst can be reused at least four additional times in subsequent reactions without considerable decrease in catalytic activity.We have synthesized 2-phenylsulfonyl-3-amino-4H-naphthopyran derivatives by threecomponent condensation of aldehyde,benzene sulfonyl acetonitrile and 1-naphthol under solvent free condition at 100℃ using potassium phthalimide(PPI)and K3PO4.3H2 O as catalyst with good yield between 83%-93% in 5min-40 min.The catalyst can be reused at least four additional times in subsequent reactions without considerable decrease in catalytic activity.