Photochemical Synthesis Of Heterocyclic Compounds

Heterocyclic compounds have extensive application in medicinal chemistry.In particular,oxygen-and nitrogen-containing heterocycles are the core structural units in pharmaceutical active molecules.In this dissertation,based on the importance of these compounds,the development for the synthesis of tryptanthrin compounds,cyclic alkenyl sulfones,fluorinated heterocyclic compounds under green and mild reaction conditions are presented.(1)Tryptanthrin compounds have many pharmacological activities,such as antibacterial,and anticancer.A series of tryptanthrin derivatives can be efficiently synthesized,with isatin and isatoic anhydride,Acid Red 94 in 5.0 mol%loading as the photosensitizer,DMF as the solvent and K2CO3 as the base were used,under the irradiation of a 23 W fluorescent bulb for 24 hours,The reaction mixture delived the desired products and the isolated yield up to 98%.In contrast to the existing methods,the present synthetic protocol with a lot of advantages,such as the mild reaction condition,low catalyst loading,simpler procedure and easy separation.(2)Sulfone,is a class of crucial organic synthetic unit.It plays a vital role in pesticide and medicine,such as anti-leprosy,and antifungal.The using of 1,6-enynes and sulfonyl chlorides and Ir(dtbbpy)(ppy)2PF6(1.0 mol%)as the photosensitizer,the reaction under the irradiation of a 23 W fluorescent bulb delived various five or six-membered heterocyclic sulfone containing compounds.C-S,C-C,C-Cl bonds were established and two different functional groups:sulfonyl group,halogen were istalled to the final product.The present ATRC process afford chloroalkyl-substituted cyclic alkenyl sulfones in full atom-economic.(3)Fluorinated compounds are widely used in all area.Described herein is a visible light driven chlorotrifluormethylative and chlorotrichloromethylative cyclization reactions approach access to the chlorotrifluoromethylated and chlorotrichloromethylated cyclic compounds.The using of 1,6-enynes and trifluoromethyl sulfonyl chloride or trichloromethyl sulfonyl chloride and Acr+-Mes(5.0 mol%)under the irradiation of a 23W fluorescent bulb and DCM was used as solvent.The photochemistry was utilized to generate the trifluoromethyl and trichloromethyl adicals and trigger the radical addition/cyclization/chlorination sequences.The corresponding pyrrolidines,piperidines and cyclopentanes were obtained in good yields with excellent regio-and stereoselectivity...