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.     

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

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.     

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.     

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.     

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.     

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.     

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].     

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.     

Anomalous nucleosides and related compounds

Amino acid and peptide derivatives of phenazinecarboxylic acids (phenazinylpeptides) have been obtained by the reaction of hydrochlorides of esters of amino acids, phosphorus trichloride, and phenazinecarboxylic acids with the subsequent splitting off of the protective ester groups in an acid or an alkaline medium.For Communication XV, see [5].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 989–990, July, 1970.     

Anomalous nucleosides and related compounds

-N₁-Glycosides of the azapyrimidine series were synthesized by reaction of trimethylsilyl derivatives of 5-amino- and 5-alkylamino-6-azauracils with protected 1-halo-substituted sugars (in benzene at room temperature for 72 h) in the presence of HgO/HgBr₂ or Hg(OCOCH₃)₂. Some of the physicochemical properties of the new anomalous nucleosides were studied.See [1] for communication XXVII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1260–1263, September, 1977.     

Anomalous nucleosides and related compounds

In order to obtain nontoxic biologically active aza analogs of pyrimidine, the synthesis of amino acid derivatives of 6-azauracil has been carried out: a) by the reaction of 5-bromo-6-azauracil (I) [1] with amino acid salts, and b) by the carbodiimide condensation of 5-amino-6-azauracil (II) [1] with benzyloxycarbonylamino acids.     

Anomalous nucleosides and related compounds

The synthesis of some nitrophenylhydrazones of products obtained by the oxidation of nucleosides with sodium periodate has been effected.For part XI, see [4].