Generation of benzocyclobutadiene derivatives from zirconaindene derivatives

Zirconaindene derivatives produced benzocyclobutadiene derivatives in situ in the presence of CuCl and 1,4-naphthoquinone, which afforded their dimers, 6a,10b-dihydrobenzo[a]biphenylenes and dibenzosemibullvalenes or dibenzo[a,e]cycloctenes.     

Benzimidazole derivatives

The alkylation of benzimidazole and its derivatives with propargyl bromide was studied. 1-(2-Propynyl)benzimidazoles are readily formed in liquid ammonia in the presence of sodium amide. The alkylation of 1-ethyl-2-aminobenzimidazole leads to a mixture of 2-(N-mono)- and 2-(N,N-2-propynyl)amino-1-ethylbenzimidazoles.See [1] for communication XXX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 551–552, April, 1973.     

Indole derivatives

It is shown that the reaction of indolealdehyde with nitroacetic acid esters leads to esters of 4-indolyl-3,5-dicarboxyisoxazoline N-oxide. 4-Indolyl-3,5-isoxazolinedicarboxylic acid N-oxide was obtained by hydrogenolysis of the dibenzyl ester.The following abbreviations are used in this paper Me methyl - Et ethyl - Bz benzyl and Ind = 3-indolyl Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1505–1507, November, 1970.     

Quinaldine derivatives

A new synthesis of substituted 2,5-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]quinolines is realized by heating the corresponding 2-methyl-3-(3-hydroxybutyl)-4-hydroxy(methoxy)-quinoline in polyphosphoric acid. The preparation of ketones of the quinoline series is described.See [1] for communication XXV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 534–537, April, 1972.     

Isoquinoline derivatives

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-4-spirocyclopentane was obtained by condensation of 3,4-dimethoxyphenyl-1-(aminomethyl)cyclopentane with formalin. The corresponding amides, which were reduced to tertiary amines, were synthesized by reaction of the latter with the acid chlorides of substituted benzoic and phenylacetic acids. Substituted dibenzo[a,-g]quinolizines, isoindolo[1,2-a]isoquinolines, and 1-(3,4-dimethoxyphenyl)-1-[(6,7-dimethoxy-1, 2,3,4-tetrahydro-2-isoquinolinyl)methyl]cyclopentane were synthesized, respectively, by condensation of 1-aryl (or aralkyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-4-spirocyclopentanes and their open analog -1-(3,4-dimethoxyphenyl)-1-(3,4-dimethoxyphenylethylaminomethyl)cyclopentane — with formalin.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 679–682, May, 1973.     

Cubane derivatives

An efficient procedure for the preparation of 1,4-bis(hydroxymethyl)cubane by reduction of cubane-1,4-dicarboxylic acid or its dimethyl ester with aluminum hydride was developed. The molecular structure of 1,4-bis(hydroxymethyl)cubane was established by X-ray diffraction analysis. For Part 3, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1387–1390, July, 1998.     

Azaindole derivatives

Electrophilic substitution reactions — cyanomethylation, bromination, nitration, and the Mannich reaction- in the 5-azaindole series were studied. It is shown that, despite the literature data, 5-azaindole behaves like the isomeric 4- and 7-azaindoles in these reactions. Conditions that make it possible to synthesize various 3-substituted 5-azaindoles in high yields were found.See [1] for communication XL.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1528–1530, November, 1972.     

sym-Triazine derivatives

The structures, tautomerism, and acid-base properties of some sym-triazinyl-substituted CH acids were studied.See [1] for Communication 6.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 241–249, February, 1988.     

Indole derivatives

New -carboline derivatives were synthesized on the basis of the reaction of 2-(-aminoisobutyl)indole with glutaric anhydride and opianic acid.See [1] for communication XLIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1630–1632, December, 1976.     

Aminophosphinidene derivatives

Abstract

Elimination and fragmentation reactions lead to carbene analogous iminophosphanes which undergo 2 + 1 addition as well as insertion reactions. Secondary aminophosphanes and amino substituted three-membered phosphorus rings are phosphinidene transfer reagents and therefore valuable building units for cyclic and acyclic compounds. Synthetic routes to amino substituted diphosphenes and their reaction behaviour are reported.     

Azaindole derivatives

An increase in the C-N bond strength in a series of N-alkyl substituents (methyl < ethyl < hexyl < butyl) was established from a study of N-dealkylation processes during the synthesis of substituted 7-azaindoles from 2,6-dichloro-3-(-chloroethyl)-4-methylpyridine and unsymmetrical alkylbutylamines.See [1] for Communication XXXV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1546–1549, November, 1970.     

Azaindole derivatives

3-Bromo-5-nitro-4-(-dimethylaminovinyl) pyridine, the reduction of which with iron filings in acetic acid led to 4-bromo-6-azaindole, was obtained from 3-bromo-4-chloro-5-nitropyridine via (3-bromo-5-nitro-4-pyridyl)malonic ester and 3-bromo-5-nitro-4-methylpyridine.See [1] for communication 55.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 86–88, January, 1979.     

Indole derivatives

Reduction of 2,2,4-trimethyl-, 2,2,4,4,6-pentamethyl-, and 2,2, 4,4,9-pentamethyl-1,2,3,4-tetrahydro-γ-carboline gives 1,2,3,4, 4a,9a-hexahydro-γ-carbolines, along with products of destructive hydrogenation. The sole reduction product of 2,2,3,4,4-pentamethyl-1,2,3,4-tetrahydro-γ-carboline is 2-(β-methylaminoisobutyl)indoline.     

Azaindole derivatives

As in the case of N-substituted anilines, trichlorocollidine forms 6-chloro-7-azaindoline derivatives rather than 6-amino-7-azaindoline derivatives with sterically hindered primary amines of the β-phenylisopropylamine type. On passing to tert-butylamine, nucleophilic attack at the α and α′ positions of the pyridine ring proves to be sterically impossible, and dehydrohalogenation of trichlorocollidine to 2,6-dichloro-3-vinyl-4-methylpyridine becomes the principal reaction.     

Azaindole derivatives

The reaction of 6-chloro-7-azaindolines with naphthyllithium and subsequent treatment with benzophenone give (7-aza-6-indolinyl)diphenylcarbinol and 6-unsubstituted 7-azaindolines, the ratios of the amounts of which are determined by the character of the substituent attached to the nitrogen atom in the 1 position of the azaindoline molecules. In the presence of acidic catalysts (1-butyl-4-methyl-7-aza-6-indolinyl)diphenylcarbinol undergoes dehydration to 1-butyl-4-methyl-6-diphenylmethyl-7-azaindole. Ideas regarding the mechanism of this reaction are expressed.See [1] for communication L.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1527–1530, November, 1977.The authors thank Yu. N. Sheinker, K. F. Turchin, L. F. Linberg, E. M. Peresleni, and T. Ya. Filipenko for conducting the spectral investigations.     

Indole derivatives

A new method for the synthesis of alkyl-substituted tetrahydro--carbolines has been developed which involves the cyclodehydration of 2-(2'-aminoisobutyl)indole and 2-(2 aminoethyl)indole with various aldehydes and ketones. The reduction with amalgamated zinc in hydrochloric acid of 2, 2-dimethyl-, 4, 4-dimethyl-, and 2, 2-dimethyl-4-phenyl-1, 2, 3, 4-tetrahydro--carbolines has been studied. The structure of the compounds obtained on reduction has been demonstrated.For part XXV, see [2].     

Indole derivatives

Reactions of α-acetamido-β-(3-indolyl) acrylic acid derivatives with some sulfur-containing compounds were carried out. Benzyl and acetyl derivatives of β-mercaptotryptophan esters were obtained.