Research On Synthesis Of Phenothiazinyl Chalcone And Its Michael Reaction

Michael addition reaction is ?,?-unsaturated ketones and active methylene compounds by 1,4-conjugated addition reaction,under alkaline conditions.This reaction is one of the simplest and most effective ways to generate C-C single bond.The multifunctional active macromolecules phenothiazine known as thiodiphenylamine or sulfur azacanth-racene was introduced into the chalcone in order to obtain phenothiazinyl chalcone.It can be reused in many areas because of its considerable reaction and biological activity.In this subject,a series of 1-phenothiazinyl-3-aryl-propenone with different types was planned and synthesized.Which carried out Michael reaction with different active methylene compounds,In this process,the molecular chain length and conjugate system of the compound have been improved.Synthesis of 10-acetyl phenothiazine.10-acetyl phenothiazine was synthesized with phenothiazine as the starting material,acetyl chloride as acylating agent and benzene as solvent.And the structures of the obtained compounds were characterized by FT-IR,~1H NMR and so on.Synthesis of 1-phenothiazinyl-3-aryl-propenone.Acetyl phenothiazine and 12 kinds of aromatic aldehydes as raw materials,in methanol solvent,NaOH catalyzed,the occurrence of aldol reaction,it can be obtained the target compounds,Which include 1-phenothiazinyl-3-phenyl-propenone,1-phenothiazinyl-3-(4-fluorophenyl)-propenone,1-phenothiazinyl-3-(4-chlorophenyl)-propenone,1-phenothiazinyl-3-(4-bromophenyl)-propenone,1-phenothiazinyl-3-(4-dimethyl-aminophenyl)-propenone,1-phenothiazinyl-3-(4-methylphenyl)-propenone,1-phenothiazinyl-3-(4-methoxyhenyl)-propenone,1-phenothiazinyl-1-(4-nitrophenyl)-propenone,1-phenothiazinyl-3-(3-nitrophenyl)-propenone,1-phenothiazinyl-3-(2-pyridyl)-propenone,1-phenothiazinyl-3-(2-thienyl)-propenone,1-phenothiazinyl-3-(2-furyl)-propenone.And the structure was characterized by FT-IR,~1H NMR and so on.At the same time,the effects of factors,such as the molar ratio of 10-acetyl phenothiazine and aromatic aldehyde,catalyst type,reaction temperature and different of substituent groups on the yield of the obtained compound was investigated by single factor experiment.The optimum synthesis conditions of phenothiazine chalcone can be obtained: the molar ratio of 10-acetyl phenothiazine and aromatic aldehyde was 1:1.1,reaction temperature was 70?,NaOH particles as catalyst,the reaction time was 30 min,the yield reached more than 85%.Study on Michael reaction of phenothiazine chalcone.1-phenothiazinyl-3-aryl-propenone respectively with acetylacetone,barbituric acid,cyclohexanone,ethyl acetoacetate,thiobarbituric acid and CH2(CN)2,CH3NO2,CH3 CN,using solvent and solvent-free solid state grinding method respectively by Michael addition reaction.And the structure of the final products was characterized by FT-IR,~1H NMR,13 C NMR and so on.At the same time,the reaction conditions of Michael reaction were optimized by the single factor experiment in the solid phase grinding method.The optimum reaction conditions were as follows: molar ratio(phenothiazinyl chalcone / active methylene compound)was 1:1.3,room temperature,grinding time of 35 min,the final product yield of up to 80% or more.