Synthesis of Indole Derivatives; Investigation mechanism of E. Fischer Reaction

Author: ioseb chikvaidze
Keywords: Pyrroloindole, Indoloquinoxaline, Pyrroloindoloquinoxaline
Annotation:

The possibility of building of a new isomeric, heterocyclic, five ring containing pyrroloindolo-quinoxaline systems on the example of the first representative 3,6-dihydropirrolo[3,2:4’5’]indolo[2,3-b]quinoxaline were studied. The key compound - 6H-indolo[2,3-b]quinoxaline and its nitrating product were obtained by the condensation of isatin and o-phenylendiamine. 1-acetyl-2,3-dihydro-5-[2’-(isonitroso)acetamido]indoline was synthesized, cyclisation of this product in conc. sulfuric acid 1H,5H-5-acetyl-6,7-dihydropyrrolo[2,3-f]indole-2,3-dione is obtained. A target heterocyclic product 1-acetyl-1H,5H-2,3-dihydropyrrolo[2’3’:5,6]¬indolo[2,3-b]quinoxaline is synthesized by the condensation of 1H,5H-5-acetyl-6,7-dihydropyrrolo[2,3-f]indole-2,3-dione and o-phenylendiamine in acetic acid. The new nitriles and binitriles: 3-cyanomethyl-2-ethoxycarbonylindole and 3,3’-bis¬cy-anomethyl-2,2’-diethoxycarbonyl-bis(indole-5-yl)-oxyde have been prepared by using indole and ethoxycarbonyl derivatives of bis-(indole-5-yl)oxide. Prepare for the new mono- and bi-analoges of gramine we used Mannich reaction – aminomethylation of indole and ethoxycarbonyl derivatives of bis-(indole-5-yl)oxide by using diethylamine, formaldehyde and acetic acid. Shown, that obtained derivatives of cyanomethyles by transformation of this compounds is possible. The structure of synthesized compounds was established by NMR, IR and mass-spectroscopy