Three Kind Of Heterocyclic Compounds’ Synthesis Via Michael-aldol Etal Reaction Catalyzed By Enzyme

Heterocyclic compounds are a class of organic compounds with biological activity and medical value.The research on theirs synthesis methods has attracted researchers’ attention in recent years.Most of effective methods have been reported,but most of them do not accord with "green chemistry".Therefore,the green synthetic route of heterocyclic compounds have been studied in this paper.The main research work includes:(1)Synthesis of 3-hydroxy-5-phenyltetrahydro-4H-thieno[2,3-c]pyrrole-4,6(5H)-dione with Michael-aldol tandem reaction catalyzed by alkaline protease.The Michael-aldol tandem reaction to achive 3-hydroxy-5-phenyltetrahydro-4H-thieno [2,3-c]pyrrole-4,6(5H)-dione of 1,4-dithiane-2,5-diol and N-phenyl maleimide catalyzed by alkaline protease was reported.Through the optimization of the types of enzyme,solvent and temperature,under 40℃ in deionized water solvent,3-hydroxy-5-phenyltetrahydro-4H-thieno[2,3-c]pyrrole-4,6(5H)-dione catalyzed by alkaline protease was obtained,the yield of the reaction reached 93% and the Dr value of 3:1 was also obtained.(2)Synthesis of 2-alkylazaarene compounds by nucleophilic addition of aromatic aldehydes and 2-methyl quinoline catalyzed by proteinase from Aspergillus melleus.After optimization the types of enzyme,solvent,temperature,enzyme quantity and so on,a green method for synthesizing 2-alkylazaarene compounds was obtained,At 60 ℃,in 50% methanol and water(v/v)solvent,Template reaction of 2-methyl quinoline with 2-nitrobenzene formaldehyde was catalyzed by proteinase from Aspergillus melleus,the yield of 60.4% was obtained.fifteen kinds of products have been developed,and the highest yield was up to 72%.(3)Synthesis of flavanones catalyzed by albumin from bovine serum: At 60℃ in the methanol solvent,flavanones synthesizing of 2’-hydroxy chalcone self cyclization catalyzed by albumin from bovine serum were observed,the highest yield reached 88.2%.seven kinds of products have been developed,and the yields of 40%-90% were achieved.