Synthesis And Characteirzation Of Novel Heterocyclic Compounds Based On Indoles

Indoles are important heterocyclic compounds and many drug molecules with goodpharmacological activity containing indole structure. For example, acetyl-substituted indolederivatives have a wide range of pharmacological activity, such as anticancer, antiviral,sterilization, anti-inflammatory and cardiovascular inhibitory activities. Thus, the synthesisand further reactions of heterocyclic compounds containing acetylindole moiety would beinteresting. So, in continuation of our previous work on the synthesis of biologically activeheterocycles and in view of the wide application of indole compounds in medicineintermediates industry，the thesis mainly focused on the synthesis and study of novel acetylindole heterocyclic compounds. This thesis is mainly divided into four parts.In the first part, the recent advance on the synthesis and application of indole and itsderivatives was reviewed.In the second part, eleven novel cinnamoyl substituted indole derivatives (3a-3k) weresynthesized in52.3-70.1%yields through the Aldol-Condensated reactions of1-(1-benzyl-2-chloro-1H-indol-3-yl)ethanone and benzaldehyde and substituted benzaldehydes using KCO3as catalyst under solvent-free condition. The structures of all the novel compounds wereconfirmed by IR, MS, and1H NMR.In the third part,3,3-dibenzylindolin-2-one (6) and1,3,3-tribenzylindolin-2-one (7) weresynthesized by unexpected nucleophilic substitution reaction of indolin-2-one and (chloromethyl)benzene in refluxing acetone in the presence of anhydrous K2CO3and KI as catalyst.Subsequently, the resulting ether6was further reacted with acetic anhydride or chloroacetylchloride using DMAP as catalyst to give the corresponding compounds9and11. Thestructure of3,3-dibenzylindolin-2-one (6) was confirmed by the X-ray crystal structure.In the fourth part,1-benzylindolin-2-one (13) was first synthesized from isatin, whichwas further reacted with acetic anhydride using DMAP as catalyst to give the intermediate3-acetyl-1-benzyl-1H-indol-2-yl-acetate in62.4%yield. The resulting intermediate wasfurther hydrolyzed to afford the corresponding1-(1-benzyl-2-hydroxy-1H-indol-3-yl)ethanone (14) in79.9%yields. The reaction of compound14with iodomethane did not givethe corresponding1-(1-benzyl-2-methoxy-1H-indol-3-yl)ethanone but afford3-acetyl-1- benzyl-3-methylindolin-2-one (17) as main product, which was characterized by spectraldata.