Synthesis And Characterzation Of Chalcone Containing Carbazole Compounds And Its Derivatives

Carbazole is a kind of important heterocyclic compounds,it has a good chemical properties,such as biological activity and photochemical properties.In addition,there is a large conjugated system in the carbazole structure,so,it has good thermal stability.In recent years,it has been used in the field of medicine and optics.Chalcone's diversity is characterized because it has free aromatic substituents at both ends.In recent years,there are few studies on the carbazolylcontaining chalcone compounds and their derivatives,and the preparation time was longer,it's harmful to the development of green synthetic chemistry.In this paper,the preparation methods of chalcone containing carbazolyl and its derivatives were discussed and studied,in ordered to make use of the organic federation of chalcone compounds containing carbazole with active hydrogen or active methylene compounds,obtained drug molecules whichhad dual antibacterial effect.In this paper,twenty kinds of chalcone containing carbazolyl compounds were synthesized by solid state grinding,on the basis of this,chalcone compounds with four kinds of compounds containing active hydrogen reacted by Michael addition,obtained eighty Michael addition products which contained carbazole groups.?1?N-methyl carbazole was synthesized.We used carbazole and dimethyl sulfate as the raw material,sodium hydroxide as catalyst,substitution reaction of dimethyl sulfate's methyl groups on carbazole's Natoms,used liquid reflux method,in the discussion of single factor orthogonal method,comparative analysis of the effects of catalyst dosage,molar ratio,reaction temperature,time and solvent on the yield oftarget product,the synthe-sis of N-methyl carbazole the optimum reaction conditions were:the molar ratio of n?carbazole?:n?dimethyl sulfate?:n?sodium hydroxide?was 1:4:9,the reaction temperature was at room temperature,the reaction time was 1h,and N-methyl carbazole's yield could reach more than 98%.The structure was verified by melting point tester,FT-IR,1H NMR and ¹³ C NMR.?2?N-ethyl carbazole was synthesized.with the carbazole and ethyl bromide as raw material,using sodium hydroxide as catalyst,by the liquid reflux method,we obtained N-ethyl carbazole.The amount of catalyst and bromoethane,reaction temperature,reaction time,and solvent had been discussed by single factor method,The best conditions for the reaction were: sodium hydroxide as catalyst,the molar ratio of n?carbazole?: n?ethyl bromide?: n?sodium hydroxide?was 1:2:4,the reaction temperaturewas 1h,the yield was above 98%.The structure was verified by meltin g-point tester,FT-IR,1H NMR,and ¹³ C NMR.?3?3-acetyl-N-alkyl carbazole was synthesized.With N-alkyl carbazole as raw material,under the catalysis of anhyd-ous aluminum chloride,occurrence of Friedel crafts acylation reaction with acetyl chloride,alkylcarbazole 3 or 9 occurred acylation reaction of monosubstituted,generating3-acetyl-N-methyl carbazole and 3-acetyl-N-ethylcarbazole.The effects of molar ratio of raw material,amount of solvent,react-ion temperature and reaction time on the reaction were discussed:n?N-alkylcarbazole?:n?anhydrous aluminum chloride?:n?acetyl chloride?was 1:1.1:1.1,the solvent was dichloromethane,the reflux temperature was controlled at 80,the stirring time was 2h,and the yield of the product was more than 79%.The structure of the target products was confirmed by FT-IR,1H NMR,¹³ C NMR.?4?Carbazole containing chalcones were synthesized.Using 3-acetyl-N-alkyl carbazole as raw material,with sodium hydroxide/potassium carbonate as catalyst,using the method of solid state grinding respectively with benzaldehyde,4-Bromobenzaldehyde,p-chlorobenzaldehyde,fluorobenzaldeh yde,p-nitrobenzaldehyde,m-nitrobenzaldehyde,p-methoxybenzaldehyde,twoamino benzaldehyde,methyl benzene formaldehyde,2-thiophene benzalde hyde ten substituted benzaldehyde condensation reactions of twenty kindsof carbazole containing chalcone compounds.And using 3-acetyl-N-alkylcar bazole and benzaldehyde reaction as an example,through the single factor orthogonal method to discuss the best reaction conditions were: n?3-acetyl-N-alkylcarbazole?:n?substituted benzaldehyde?:n?sodium hydroxid/potassium carbonate?was 1:1.2:1.2,grinding time with 15-20 minutes,production rate was 85%-90%.The structure of the target products was confirmed by FT-IR,1H NMR and ¹³ C NMR.?5?Carbazole containing Michael adducts were synthesized.Using car bazole containing chalcone as raw material,with sodium hydroxide as catalyst,with anhydrous ethanol as solvent,with ethyl acetoacetate,cyclohexan one,ethyl malonic acid two,acetyl acetone Michael addition reaction,obta ined eighty novel carbazole containing Michael adducts.Chalcone with car bazole and ethyl acetoacetate as an example,using the single factor method to discussed the optimum reaction conditions were: n?carbazole chalcon e?:n?ethyl acetoacetate?:n?sodium hydroxide?=1:2:2,the grinding time was about two 2h-3h,the product yield was between 70%-90%.The structure of the target products was confirmed by FT-IR,1H NMR,and ¹³ C NMR.