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

It was shown that it is possible to introduce an ethynyl group into an indole ring by the acetylenic cleavage of an acyl derivative of a base. 1-Methyl-5-nitro-2-ethynylindole was obtained from 1-methyl-5-nitro-2-indolcarboxylic acid, and a series of mono- and diaminomethyl derivatives was prepared by the Mannich reaction.Communication 131 [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1472–1475, November, 1988.     

Indole derivatives

The Fischer condensation of arylhydrazones of 2, 2, 5, 5-tetramethyl-pyrrolid-3-one has given 1, 1, 3, 3-tetramethyl-7, 8-benzo-1, 2, 3, 4-tetrahydropyrrolo[3, 4-b]indole and 1, 1, 3, 3, 7-pentamethyl-1, 2, 3, 4-tetrahydropyrrolo[3, 4-b]indole. On Clemmensen reduction of the latter, the pyrrole ring undergoes degradation.     

Indole derivatives

The Fischer cyclization of arylhydrazones of 1,3-dimethyl-, 1, 3, 5-trimethyl-, and 1, 3, 6-trimethyl-4-piperidones is examined. An unusual duration of the reaction is found, resulting in rearrangement products (1, 2, 3, 4-tetrahydropyrimido[3,4-a]indoles). It is shown that hydrogenation of the latter gives 2-(-dimethylaminoalkyl)-3-methylindoles.For Part XXX, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1219–1224, September, 1970.     

Indole derivatives

The Claisen condensation of methyl 3-indolylacetate with dimethyl carbonate, methyl benzoate, methyl formate, and methyl acetate proceeds with acylation of the CH₂ group. Only the carbomethoxy group attached to the nitrogen atom of the indole ring is retained. The corresponding 5-(3-indolyl)pyrimidines were obtained by condensation of thiourea and acetamidine with the products of acylation of methyl 3-indolylacetate with methyl formate and methyl acetate.See [1] for Communication 118.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 55–58, January, 1980.     

Indole derivatives

By expanding the ring of 1-methyl-4-piperidone with diazomethane we have obtained 1-methyl-1-azacyclopentan-4-one. The Fischer cyclization of arylhydrazones of 1-methyl-1-azacyclopentan-4-one has given 3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole and a number of its derivatives for the first time. The structure of the compounds obtained was shown by a study of their PMR spectra and also by a number of chemical reactions.     

Indole derivatives

Indolylalkyldithiocarbamates were obtained by reaction of indolylalkylamines with carbon disulfide and sodium hydroxide. Their effect on pathogenic bacteria and fungi was investigated.See [1] for Communication XCVII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1371–1374, October, 1974.     

Indole derivatives

The cyclization of 1-R-2-(-aminoisobutyl)indoles with various cyclic ketones forms imines or spiro compounds of the 1,2,3,4-tetrahydro--carboline series, depending on the conditions and the structure of the ketone.For communication XL, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp 942–944, July, 1973.     

Indole derivatives

The Wittig reaction with indole-3-aldehyde and its N-acetyl derivative has been studied. Data are presented on the influence of various factors on the formation of the unsaturated compound. Some hypotheses are put forward concerning the reactivity of indole-3-aldehydes under the conditions of this reaction. The previously unknown -(indol-3-yl)--phenylethylene has been obtained with a yield of 54%.For part XXXIV, see [15].     

Indole derivatives

The Fischer condensation of arylhydrazones of 2, 2, 5, 5-tetramethyl-pyrrolid-3-one has given 1, 1, 3, 3-tetramethyl-7, 8-benzo-1, 2, 3, 4-tetrahydropyrrolo[3, 4-b]indole and 1, 1, 3, 3, 7-pentamethyl-1, 2, 3, 4-tetrahydropyrrolo[3, 4-b]indole. On Clemmensen reduction of the latter, the pyrrole ring undergoes degradation.For Part XXIX, see [1].     

Indole derivatives

A new one-step method was developed for the preparation of 3-indolyl isothiocyanates by reaction of 3-aminoindoles with carbon disulfide in the presence of sodium ethoxide. It is shown that indolo[2,3-d]-1,3-thiazines are obtained from 3-aminoindoles and carbon disulfide when extraneous bases are absent. The structures of the compounds are confirmed by data from their IR, UV, PMR, and mass spectra.See [1] for communication CXVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1497–1503, November, 1978.     

Indole derivatives

A mixture of isomeric 2,2,4-trimethyl- and 2,4,4-trimethyl-1,2,3,4-tetrahydro--carbolines is formed as a result of the Fischer cyclization of 2,2,6-trimethyl-4-piperidone arylhydrazones.See [1] for communication XXXVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1070–1073, August, 1971.