Indole derivatives

The reaction of substituted aziridines with indole was studied. It is shown that the presence of electron-donor substituents attached to the carbon atom or of bulky substituents attached to the nitrogen atom in aziridines favors cleavage of the aziridine ring by indole to give derivatives of tryptamine and tryptophan.For Communication VI see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1066–1069, August, 1974.     

Indole derivatives

A method for the preparation of α-(3-indolyl) aliphatic acids, including those containing functional groups (COOH, C≡N), which is based on alkylation of N-carbomethoxy-3-indolylcyanoacetic ester, was developed.     

Indole derivatives

It has been established that the cyclization of arylhydrazones of 3-(-ethoxycarbonylethyl)1-methylpiperidin-4-one is accompanied by a rearrangement and leads to a 1,2,3,4-tetrahydropyrimido[3,4-a]indole derivative [1], The cyclization of arylhydrazones of 2-(-methoxycarbonylethyl)cyclohexanone under the same conditions forms indole and 3H-indole derivatives.For Communication XXXI, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 927–930, July, 1970.     

Indole derivatives

Benzylthio(skatyl)malonic ester has been synthesized by the condensation of gramine in toluene or its methiodide in ethanol with benzylthiomalonic ester, and this has been converted by monodecarboxylation and debenzylation with sodium in liquid ammonia into DL--mercapto--(indol-3-yl)propionic acid [-(3-indol-yl) thiolactic acid]. DL--Benzylmercapto--(indol-3-yl)propionic acid has also been obtained from methyl DL--bromo--(indol-3-yl)propionate and benzyl mercaptan. Alkaline hydrolysis of S-[-(indol-3-yl)--methoxycarbonylmethyl]thiouronium bromide has led to ring closure with the formation of 5-skatylthiazolidine-2, 4-dione.For part XLVIII, see [1].     

Indole derivatives

The Fischer condensation of 1-methyl-3-piperidone with arylhydrazines, which is accompanied by side processes, leads to the corresponding 1,2,3,4-tetrahydro--carbolines.See [1] for communication XXXVII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 81–83, January, 1972.     

Indole derivatives

5-(3-Indolylmethyl)barbituric and 5-(3-indolylmethyl)thiobarbituric acids were obtained by condensation of 3-indolylmethylmalonic ester with urea and thiourea in monoglyme (1,2-di-methoxyethane) in the presence of lithium methoxide. The first of the two acids was also obtained by catalytic hydrogenation of 5- (3-indolylmethylene)barbituric acid.     

Indole derivatives

An improved method is proposed for obtaining skatyl- and substituted skatylmalonic esters by the alkylation of sodiomalonic esters with gramme methiodide in dimethylformamide in an inert-gas atmosphere, which leads to yields exceeding 90%. To obtain a skatylmalonic ester uncontaminated with the diskatylmalonic ester a method is proposed which involves the catalytic hydrogenation of a skatylidenemalonic ester over Pd/CaCO₃; yield 96%.For Communication LXXXVI, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1512–1514, November, 1973.     

Indole derivatives

New condensed systems (VII–XVI), the structures of which were confirmed by the PMR spectra, were synthesized by the Fischer reaction of 2-methyl-5-hydrazinofuran, 2,3-dimethyl-5-hydrazinobenzofuran, and 2-methyl-8-hydrazinobenzofuro[3,2-c]pyridine with methyl ethyl ketone, methyl propyl ketone, cyclohexanone, 1-methyl-4-piperidone, and tetrahydro-4-thiopyrone.See [1] for communication XXXIX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp.1075–1078, August, 1972.     

Indole derivatives

The Fischer cyclization of arylhydrazones of 1-butyl-, 1-benzyl-, and 1-cyclohexyl-3-pyrrolidinones has been studied, as a result of which a synthesis of 1, 2,3,4-tetrahydropyrrolo[3,4-b]indoles has been developed. The structure of the compounds obtained has been confirmed by their UV and NMR spectra and by a number of chemical properties.     

Indole derivatives

A method is described for the preparation of -(3-indolyl)acrolein. Oximation of this followed by dehydration gives -(3-indolyl)acrylonitrile. Reduction gives -(3-indolyl)allyl alcohol.For part XXXII, see [1].     

Indole derivatives

The synthesis of-glycerides of 3-indolyl carboxylic acids has been effected by the reaction of 3-indolyl carboxylic acids with benzylideneglycerol in the presence of dicyclohexylcarbodiimide with the subsequent elimination of the benzylidene group by hydrogenolysis. The- and-glycerides have been separated by paper chromatography.For communication XXX, see [1].     

Indole derivatives

The Fischer cyclization of arylhydrazones of 4-thiepanone leads to 1, 3, 6H, 4, 5-dihydrothiepino[4, 3-c]indoles, while the cyclization of arylhydrazones of the S, S-dioxide of 4-thiepanone forms 6H-1, 2, 4, 5-tetrahydrothiepino[5, 4-c]indole.For communication XXIV, see [1].     

Indole derivatives

5-Substituted (butyl, phenyl)-5-skatyl(5-methoxyskatyl)barbituric acids were obtained by alkylation of the corresponding barbituric acids with gramine and 5-methoxygramine in dimethylformamide and dimethyl sulfoxide. 5,5-Dialkylation products were obtained in the alkylation of barbituric and thiobarbituric acids with gramine.     

Indole derivatives

The influence of dehydrogenating dehydrating (deaminating) additives on the composition and yield on the products of the cyclization of N-(-hydroxyethyl)aniline and N,N-diphenylethylenediamine has been studied. The closure of the indole and pyrrole rings takes place through the dehydration and deamination, respectively, of the starting material on oxide catalysts. A reaction scheme explaining the formation of all the products observed has been suggested.For Communication L see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 6, pp. 766–769, June, 1970.     

Indole derivatives

1-Carbomethoxy-3-indolylcyanoacetic ester reacts with amidines, guanidine, and thiourea to give, respectively, 2-alkyl- and 2-aryl-5-(3-indolyl)-4-amino-6-hydroxypyrimidines and 2-amino- and 2-thio-5-(3-indolyl)-4-amino-6-hydroxypyrimidines.See [1] for communication CVIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1513–1515, November, 1976.     

Indole derivatives

A new heterocyclic system — 12H-6,7-dihydrobenz[2,3]oxepmo[4,5-b] indole — and a number of its substituted derivatives were synthesized by Fischer cyclization of 5-homochromanone arylhydrazones.See [1] for communication XXXIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 65–67, January, 1971.     

Indole derivatives

The reaction of gramine methiodide with the sodium or potassium derivatives of -oxo sulfoxides leads to the formation of skatyl-substituted sulfoxides. When the latter are cleaved with amalgamated aluminum, skatyl-substituted ketones are obtained.For Communication V, see [4].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1069–1070, August, 1970.     

Indole derivatives

3-Aminoindole was obtained by the action of alkali on its hydrochloride in a reductive medium. Acylation of 3-aminoindole with acetic anhydride gave its mono-, di-, and triacetyl derivatives, whereas reaction with p-substituted benzenesulfonyl chlorides gave the corresponding N-3-indolylsulfonamides. The reaction of 3-aminoindole with aromatic aldehydes gives Schiff bases.See [1] for communication CXII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 481–485, April, 1977.     

Indole derivatives

The behavior of some 3-nitrovinyl indoles in their reactions with nitrogen-containing nucleophilic reagents is examined. It is shown that hydroxylamine, phenylhydrazine, hydrazine, and semicarbazide react with 3--nitrovinyl indole to give the corresponding oxime, phenylhydrazone, azine, and semicarbazone of indole-3-aldehyde, possibly by decomposition of intermediates formed by the addition of the nucleophilic reagents to the nitrovinyl indole. 3--Nitropropenyl indole and N-methyl-3--nitrovinyl indole react similarly. Only the addition products of phenylhydrazine with N-acetyl-3-nitrovinyl indole and N-acetyl-3--nitropropenyl indole are stable. The reaction conditions and constants of the compounds prepared are given, and explanations are offered for the results obtained.For part XXXV, see [14].