Hydroacridines and related compounds

The stereochemistry of the hydride reduction of N-substituted 4a-cyano-, 4a,10a-dicyano-, and 4a,10a-peroxy-9-phenylperhydroacridines was studied. The configuration of a series of isomeric N-substituted 9-phenylperhydroacridines was established.See [1] for communication XIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 508–512, April, 1977.     

Hydroacridines and related compounds

Some N-aryldecahydroacridines reduce N=N, C=N, C=O, NO₂, and acridine groups in acidic media. In neutral media, N-aryldecahydroacridines are oxidized by caloranil and polyhaloalkanes.     

Hydroacridines and related compounds

One hydrogen atom is replaced by lithium in the reaction of 1,2,3,4-tetrahydroacridine and sym-octahydroacridine with phenyllithium; effective replacement of a second hydrogen atom by lithium becomes possible after replacement of the first lithium by an alkyl group. This makes it possible to achieve step-wise alkylation.See [1] for communication VIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 673–675, May, 1972.     

Hydroacridines and related compounds

2-Phenyl-7,7-dimethyl-5H-7,8-dihydropyrano[4,3-b]pyridine and its N-oxide were synthesized. Refluxing of the latter with acetic anhydride gives 2-phenyl-7,7-dimethyl-8-hydroxy-5H-7,8-dihydropyrano[4,3-b]pyridine acetate; hydrolysis of the acetate gives the alcohol.See [1] for communication XII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 824–825, June, 1973.     

Hydroacridines and related compounds

The effect of substituents in the 9 and 10 positions on the reductive capacities of 9,10-disubstituted decahydroacridines was established in the case of the reduction of organic dyes (Methylene Blue, Indigo Carmine, and Brilliant Green).See [1] for communication XV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 969–972, July, 1977.     

Hydroacridines and related compounds

3,3-Dimethyl-2-oxa-1,2,3,4-tetrahydroacridine and its N-oxide and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydroacridine N-oxide were synthesized. On heating with acetic anhydride, the N-oxides form, respectively, acetates of 3,3-dimethyl-2-oxa-1,2,3,4-tetrahydro-4-acridinol and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol. Hydrolysis of the acetates gives the alcohols themselves. Oxidation of 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol acetate gives the corresponding N-oxide. Oxidation of 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol with manganese dioxide gives 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinone.See [9] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1218–1221, September, 1971.     

Hydroacridines and related compounds

The N-oxides of 2,4-diphenyl-5,6,7,8-tetrahydroquinoline, 2,4-diphenylpyrindane, and 7,7-dimethyl-2,4-diphenyl-6-oxa-5,6,7,8-tetrahydroquinoline were synthesized. On heating with acetic anhydride, the N-oxides form, respectively, acetates of 2,4-diphenyl-5,6,7,8-tetrahydro-8-quinolinol, 2,4-diphenyl-7-pyrindanol, and 7,7-dimethyl-2,4-diphenyl-6-oxa-5,6,7,8-tetrahydro-8-quinolinol; hydrolysis of the acetates gives the alcohols.See [10] for communication X.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1547–1551, November, 1972.     

Hydroacridines and related compounds

4-Benzoylhydroacridines were synthesized by the reaction of 4-lithiohydroacridines with benzonitrile or benzoyl chloride. Their capacity for keto-enol tautomerism was noted.See [1] for communication IX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 7, pp. 984–986, July, 1972.     

Hydroacridines and related compounds. 20. Reduction of organic compounds by 10-substituted decahydroacridines

The reduction of benzil, chalcone, and acridine with 9-phenyl-10-benzyl- and 9,10-diphenyldecahydroacridines in acidic, neutral, and alkaline media was investigated. p-(10-Decahydroacridinyl)benzoic acid salts were obtained and were used to reduce a number of organic compounds under mild conditions in close-to-neutral media.See [1] for Communication 19.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 95–98, January, 1981.     

Hydroacridines and related compounds. 22. Synthesis of compound with 2,6-epidioxypiperidine structure

The addition of hydrogen peroxide to a series of 1,4-dihydropyridine derivatives proceeds with the formation of derivatives of 6,7-dioxa-8-azabicyclo[3.2.1]octane. Such compounds may be obtained by the reaction of alicyclic 1,5-diketones with amines and hydrogen peroxide.For Communication 21, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 89–94, January, 1985.     

Hydroacridines and related compounds. 23. Caprolactam derivatives and hydrocoumarins from 4a,10a-epidioxyperhydroacridines

The thermolysis of 10-R,9-R¹,9-R²-4a,10a-epidioxyperhydroacridines has given 1-R-3-[-(2-oxocyclohexyl)alkyl]hexahydroazepin-2-ones which have been reduced to the corresponding 2-hydroxycyclohexyl derivatives. Hydrolysis of the compounds obtained led to 3-[-(R-amino)butyl]hydrocoumarins.For communication 22, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 650–656 May, 1985.     

Hydroacridines and related compounds. 21. Synthesis of 2-(2-thienyl)hydroquinolines and 2,7-dithiahydroacridines

A number of sulfur-containing 1,5-diketones were synthesized and subjected to reaction with primary amines to give derivatives of 2-(-thienyl)hydroquinolines and 2,7-dithiahydroacridines that contain 1,4-dihydropyridine and benzoxazolinotetrahydropyridine structures. The oxidation of some of the dihydropyridine derivatives was studied.See [1] for Communication 20.Translated from Khimiya Geterotsiklicheskik Soedinenii, Vol. 4, pp. 471–474, April, 1981.     

Hydroacridines and related compounds 19. Angular hydride reductions in the hydrobenz[c]acridine and hydroacridine series

The hydride reduction of dihydro- and tetrahydropyridine derivatives and of angular nitriles in the hydrobenz[c]acridine and hydroacridine series, and also the reductive cleavage of the azoline and azine rings in 11a,12-benzoxazolino- and 11a,12-benzoxazinohydrobenz[c]acridines and 4a,10-benzoxazolinohydroacridines has been studied. The stereospecificity of all the reactions mentioned has been established.For communication 18, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 508–513, April, 1980.     

Benzoxazines and related compounds

The reaction of 2-mercapto(and benzylthio)-α,α-dialkylbenzyl alcohols with nitriles under the influence of acids serves as a method for the synthesis of 2,4,4-trisubstituted 4H-1,3-benzothiazines.     

Gibberellins and related compounds

Conclusions A study was made of the photochemical aromatization of the 2-keto derivative of gibberellic acid in various solvents. Unusual fragmentation of the B ring, with the formation of the seco-structure, was observed when the reaction was run in benzyl alcohol.Deceased.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2037–2040, September, 1971.     

Benzoxazines and related compounds

Interconversion of 2-alkyl-4,4-diethyl-4H-1,3-benzoxazines and N-acyl-,-diethyl-o-hydroxybenzylamines was accomplished, and it is shown that cupric ion catalyzes these reactions.See [1] for Communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1465–1466, November, 1970.     

Benzoxazines and related compounds

The action of a nitrating mixture on 2-substituted 4,4-diethyl-4H-1,3-benzoxazines gives the corresponding 6-nitro derivatives, which can be isolated as such or as the hydrolysis products –N-acyl-,-diethyl-2-hydroxy-5-nitrobenzylamines. The latter cyclize to the corresponding 4H-1,3-benzoxazines under the influence of perchloric acid.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 303–305, March, 1972.     

Benzoxazines and related compounds

A simple method has been elaborated for synthesizing 2-substituted 4,4-dialkyl-4H-1, 3-benzoxazines by the interaction between nitriles and o-oxyphenyldialkylcarbinols under the influence of acids.For part I, [1].