Bisindoles 34. Preparation and reactions of dehydrazides of the benzo[e]pyrrolo[3,8-g]-indole and indolo[4,5-e]indole series

Summary 2, 9 -Di (carbohydrazide)-1 H, IOH-benzo[elpyrrolo[3, 2-g]indole and 2, 9-di (carbohydrazide)-3H, 8H-indolo[4, 5-e]indole have been prepared. Nitrosation of the dihydrazides has been effected. The aryl azides do not undergo the curtius rearrangment.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1048-1051, August, 1994.Communication 33, see [1].     

Bisindoles. 14. Electrophilic substitution reactions in the di(5-indolyl) oxide series

Chemistry of Heterocyclic Compounds - Some electrophilic substitution reactions in the di(5-indolyl) oxide series were studied. The Vilsmeier and Mannich reactions and diazo coupling and...     

Bisindoles. 18. Some electrophilic substitution reactions in the 1,2-di(indol-5-yl)ethane series

A quantum-chemical calculation has been made and the laws of the electron-density distribution in the molecule of 1,2-di(indol-5-yl)ethane have been determined. The electrophilic substitution reactions most characteristic for it have been studied.For communications 15–17, see [1–3].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 73–77, January, 1984.     

Pyrroloindoles. 6. New synthesis of 1H, 5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole

Ethyl pyruvate 1-acetyl-5-indolinylhydrazone was obtained by diazotization of 1-acetyl-5-aminoindoline with subsequent reduction of the diazonium salt and condensation of the hydrazine with ethyl pyruvate. A mixture of hydrogenated derivatives of linear and angular pyrroloindoles is formed as a result of cyclization of the hydrazone in polyphosphoric acid esters. Subsequent hydrolysis, decarboxylation, and dehydrogenation lead to 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo-[3,2-e]indole.See [1] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 504–507, April, 1982.     

Pyrroloindoles. 16. Some electrophilic substitution reactions of 2,7-dicarbethoxy-1H,6H-pyrrolo[2,3-e]indoles

Electrophilic substitutions of 2,7-dicarbethoy-1H,6H-pyrrolo[2,3-e]indole (Friedel-Crafts acylation, nitration, bromination) take place both at position 3 of the indole ring and at positions 5 and 8 in the benzene ring.For communication 15 see [1].Iv. Dzhavakhishvili State University, Tbilisi 380028. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1197–1201, September, 1994. Original article submitted July 5, 1994.     

1,7-migration of benzyl group in 2-substituted N-benzylindoles

It has been shown that when 2-substituted N-benzylindoles are heated above 100°C in polyphosphoric acid, the benzyl group is split off and undergoes 1,7-migration.Iv. Dzhavakhishvili Tbilisi, State University, Tbilisi 380028. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 611–615, May, 1997.     

Bisindoles. 32. Some activated diesters of 2,2-dihydroxycarbonyl-bis-(5-indolyl)sulfone and polyamides based thereon

Di-acyl halides of 2,2-dihydroxycarbonyl-bis(5-indolyl)sulfone, p-nitro-, pentachloro-, and 2,4-dinitrophenol have been used for the synthesis of activated diesters, polycondensation of which with diamines of different structures yielded polyamides containing indole fragments with free positions.For Communication 31, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1200–1202, September, 1993.     

Pyrroloindoles. 2. Some electrophilic substitution reactions in the 1H, 6H-pyrrolo[2, 3-e] indole series

As expected, the 3 and 8 positions are the reaction centers of 1H, 6H-pyrrolo-[2, 3-e] indole in the Vilsmeier-Haack and Mannich reactions. Diazo coupling takes place primarily in the 3 position and leads primarily to monosubstitution products. 6,8-Diacetyl-1H,6H-pyrrolo [2,3-e]indole and 1,8-diacetyl-1H, 6H-pyrrolo-[2,3-e] indole were isolated from the acetylation products.See [1] for communication 1.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 639–644, May, 1980.