Synthesis Of Indole-containing Heterocyclic Compounds

Organic compounds containing nitrogen distribute quite abroadly. To synthesize newheterocyclic compounds is a major channel for searching for new bioactive substances.Therefore, new synthesis of their derivatives and development of simple and convenientapproaches are desired. The thesis focused on the synthesis of heterocyclic compounds whichbased on the skeleton of quinoline and indole.The first part of the paper, summary of the biological activity, and methods of synthesis ofthiazole compounds of the indole ring.The second part, on the N-alkyl isatin reduction, acylation, and hydrolysis reactions werestudied. In one isatin N, N-dimethylformamide (DMF) as a solvent is reacted with ahalogenated hydrocarbon with12-24h to give a yield of92-98%N-alkyl isatin (2a-2d),2a toobtain1-hydrlindolin-2-one (3a-3d) by reduction with hydrazine hydrate,3a-3d via aceticanhydride and DMAP and hydrolysis catalyzed acylation yield of85-93%sodium hydroxide ina mixed solvent, tetrahydrofuran a N-hydrocarbyl-3-acetyl-2-oxindole (4a-4d). N-alkyl isatin(2a-2d) in1,4-dioxane and thiosemicarbazide reaction of N-hydrocarbyl-3-hydroxy-indol-S-triazine and (5a-5d).The third part, chapter study5-(2-chloroacetyl)indolin-2-one as substrates with thioureaand thioamide be Handseh reaction oxindole bithiazole structure of the compound. Thechloroacetyl oxindole Reaction conducted to give5-(2-chloroacetyl)indolin-2-one6, thesubstrate6in tetrahydrofuran (THF) and ethanol solvent with a substituted thioamide andthiourea reflux conditions to67%-to give83%yield of5-(5-hydrocarbyl-2-)oxindole (7a-7p).The fourth part of this chapter is mainly on N-alkyl-oxindole C-3position of doublesubstitution reaction occurs on. With N-alkyl-oxindole (3a-3d) as a substrate, the solvent DMFunder base-catalyzed conditions KOH, and alkyl halides in the C-3position for hydrocarbondisubstituted, six kinds of C-3to give bit dual-substituted compounds3,3-dihydrocarbyltin-oxindole (8a-8h).The fifth part, this chapter of N-methyl-6H-indole [2,3-b]quinolin-11-Synthetic studiesacid.1-(2-methoxy-1-methyl-1H-indol-3-yl)ethanone as a substrate9, and the isatin in10%ethanol-water to the reaction system in a yield of32.3-78.2%8kinds of twosynthetic-hydrocarbon-6-methyl-6H-indole[2,3-b] quinolin-11-carboxylic acid (10a-10h).Improvement of the above method, in the reaction system to10%methanol-water for a yield of41.9-74.6%, improves the yield, reduce the generation of byproducts.The structure of all novel compounds2a-2d,3a-3d,4a-4d,5a-5d,6,7a-7p,8a-8e,9,10a-10h were confirmed by IR,1H NMR, MS and Elementary analysis. And fluorescencespectrometry compound10a-10h.