Application Research Of Isatin And Substituted Isatins In The Synthesis Of Novel Heterocyclic Compounds

Isatins are important heterocycles, existing in a lot of plants and marine organisms.Due to their great application in the dye industry, medicine yield, and chemical pesticides,as well as utilization as biological growth promoters and chemical analysis reagents, isatinand its derivatives are now attracting more and more interest from organic syntheticchemists. In view of these foundings, in the present thesis we mainly described a facilesynthesis of a series of novel and interesting heterocyclic compounds.frim isatin andsubstituted isatins as raw materials.In the first part, on the basis of a survey of previous literatures concerning thesynthesis, applications and properties of isatins, we reviewed the recent advances on theirapplications in organic synthesis chemistry.In the second part, the1-(2-chloro-1-(4-chlorobenzyl)-1H-indol-3-yl)ethanone (2) wasselected as raw materials in the presence of ethanol sodium as catalyst to synthesize1-(1-(4-chlorobenzyl)-2-ethoxy-1H-indol-3-yl)ethanone (3) in71.5%yield. Then theresulting1-(1-(4-chlorobenzyl)-2-ethoxy-1H-indol-3-yl)ethanone (3) was further reactedwith substituted isatins (1a-1e) to give6-(4-chlorobenzyl)-6H-indolo[2,3-b]quinoline-11-carboxylic acid (4a-4e) in47.8-57.5%yields. The structures of compounds4a-4e andintermediates5a-5e were confirmed with the help of spectral data and elementary analysis.In the third part, isatin and substituted isatins (1a-1e) were choosed as the substrates toreact with the2,6-diacetyl pyridine (6) in10%ethanol-water system with KOH as thecatalyst to afford novel heterocyclic structures bearing three nitrogen quinoline acid organicligandsIn the fourth part,5-phenyl-1H-pyrano[3,4-b]quinolin-4(3H)-one (12) was firstlysynthesized from2-amino-benzophenone as starting material. And then the latter wasreacted with isatin and substituted isatins (1a-1e) in10%ethanol-water system throughPfitzinger reaction to afford polycyclic fused heterocyclic compounds (13a-13e) in50.2-60.4%yields.In the fifth part, we choosed4-acetylpyridine14as the substrate to react with theisatins (1a-1e) to afford organic ligands containing pyridine associatedquinolinecarboxylates (15a-15e).