Synthesis and properties of sym-triazine derivatives. 6. Synthesis of 2-amino- and 2,4-diamino-sym-triazines containing sterically hindered phenol segments

2-Amino-4,6-disubstituted-sym-triazines containing sterically hindered phenol segments were synthesized by cyclocondensation of N-acrylguanidines with nitriles or thiocyanates. The same compounds can be obtained by condensation of N-acylguanidine with iminoester hydrochlorides. The reaction of methyl -(4-hydroxy-3,5-di-tert-butylphenyl)propionate with biguanides gives N-substituted 2,4-diamino-6-R-sym-triazines that contain a shielded phenol residue.For Communication 5, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1392–1397, October, 1987.     

Synthesis and thermal decomposition of haloalkoxy-sym-triazines

The reaction of 4,6-bis[alkyl(dialkyl)amino]- or (4-alkylamino-6-dialkylamino-sym-triazin-2-yl)trimethylammonium chlorides with ethylene chlorohydrin and the action of phosphorus pentachloride on 2--hydroxyethoxy-sym-triazines give 2--chloroethoxy derivatives of sym-triazine, which on heating are converted to imidazo[1,2-a]-sym-triazine derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 262–265, February, 1977.     

Synthesis of 4-thiouridine derivatives

The thionation of a protected uridine with the aid of P₂S₅ has given the corresponding 4-thiouridine derivatives, which have been phosphorylated at the 5 or the 2(3)hydroxyl. On being heated in aqueous pyridine solution with liquid hydrogen sulfide, cytidine phosphates also form 4-thiouridine phosphates. 4-Thiouridine 2,3-cyclophosphate has been obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 996–1000, July, 1973.The authors thank M. Ya. Karpeiskii for his constant interest in the work and for valuable critical observations.     

Synthesis of hydrophobic derivatives of muramyldipeptides

Methyl esters of the cyclohexyl-, phenethyl-, (2-naphthyl)methyl-, and 2-(1-naphthyl)ethyl -glycosides of N-acetylmuramyl-L-analyl-D-isoglutamine have been synthesized. The corresponding glycosides of N-acetylglucosamine were obtained by glycosylating the alcohols with the peracetate of -glucosaminyl chloride in the presence of HgI₂, followed by deacetylation. Subsequent benzylidenation and alkylation with -L-chloropropionic acid led to glycosylmuramic acids, the condensation of which with the dipeptide and final debenzylidenation gave the desired glycopeptides.Simferopol' State University, 333036, Ukraine, Crimea, Simferopol', ul. Yaltinskaya, 4. Translated from Khimiya Priodnykh Soedinenii, Vol. 33, No. 1, pp. 79–86, January–February, 1997.     

Synthesis ofα-nitromethylpyridine and derivatives

-Nitromethylpyridine and -nitromethyl-ß-ethylpyridine are obtained by treating the corresponding nitrophthalones with 10% aqueous alkali. Treatment of the compounds with bromine gives the hydrobromides of the dibromo derivatives, which on treatment with aqueous sodium bicarbonate solution give the corresponding bases. Addition products of -nitromethylpyridine at the double bond of chalcone and 2-benzylidenindan-1,3-dione were obtained.     

Two paths for the formation of pyrimidines from sym-triazine

The reaction of sym-triazine with the hydrochlorides of N-unsubstituted enaminones gives mixtures of 4-alkyl-5-acyl(ethoxycarbonyl)pyrimidines and 2,6-dialkyl-3,5-diacyl(ethoxycarbonyl)pyridines. The reaction mechanism was studied by means of the ¹⁵N-labelled compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1243–1249, September, 1992.     

Synthesis of amino derivatives of quinoline and 5, 6-benzoquinoline

3-Aminocinchophen and 2-phenyl-3-aminoquinolines were synthesized by the reaction of isatin and 5-, 6-, and 7-methylisatins with -aminoacetophenone in alkaline media. A number of 3-amino-5,6-benzoquinoline derivatives were obtained by the condensation of azomethines from aromatic aldehydes and -naphthylamine with -aminoacetophenone.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 525–526, April, 1972.     

Synthesis of derivatives of the androstane series

Summary Hydrazones and symmetrical dihydrazones of 2-methyltestosterone and its 17-methyl and 17-ethyl derivatives have been synthesized.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 5, pp. 354–359, 1966     

Synthesis and properties of derivatives ofsym-triazine. 15. Synthesis of amine derivatives ofsym-triazine that contain indole groups

By the cyclocondensation of imino esters of acids of the indole series with N-acylguanidines, 2-amino-4,6-disubstituted sym-triazine are obtained that contain indole groups. The reaction of N-(indolyl-3-imidolyl)-guanidine with esters of carboxylic acids leads to 2-amino-4-(3-indolyl)-6-substituted sym-triazines. Indolyl-containing N-subsitituted 2,4-diamino-sym-trizines are synthesized by the reaction of imino esters of indole acids with biguanides. Similar products are also formed when 2-amino-4-trichloromethyl-sym-triazines that contain indole substituents react with dimethylamine, morpholine, or furfurylamine.I. M. Gubkin State Petroleum and Gas Academy, Moscow, 117917. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–223, February, 1995. Original article submitted December 21, 1994.     

Indole derivatives. 128. Synthesis and properties of 5,6- and 4,5-ethylenedioxyindoles

Reaction of 3,4-ethylenedioxyphenyldiazonium chloride with ethyl 2-methylacetoacetate and subsequent cyclization of the 3,4-ethylenedioxyphenylhydrazone of ethyl pyruvate gives a 14 mixture of 4,5- and 5,6-ethylenedioxy-2-ethoxycarbonylindoles, respectively, from which 4,5- and 5,6-ethylenedioxyindoles are formed by subsequent hydrolysis and decarboxylation. Mannich and Vilsmeyer reactions as well as acetylation and azo coupling have been studied for 5,6-ethylenedioxyindole.For Communication 127, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1624–1628, December, 1986.     

Synthesis of new arylidene derivatives of 3-aminorhodanine

The synthesis of new arylidene derivatives of 3 -aminorhodanine has been effected. It has been established that the condensation of 3-aminorhodanine with aldehydes in an alcoholic medium gives 3-arylidene derivatives. Similar reactions in an ammoniacal medium lead to 5-derivatives of 3-aminorhodanine. 3, 5-Diarylidene derivatives can be obtained by condensing 3-aminorhodanine with an excess of an aldehyde in glacial acetic acid, except for the salicylidene and 9-anthrylidene derivatives, the synthesis of which can be carried out only in two stages.     

Synthesis of derivatives of 1, 2, 3, 4-tetrahydro-4-azafluoren-3,9-diones

Cyclization of amides of -carbamido--(indan-1, 3-dione-2-yl) hydrocinnamic acid gives 1-aryl-2-carbamido-1, 2, 3, 4-tetrahydro-4-azafloren-3, 9-dione. Alkaline and acid hydrolysis of these compounds are investigated.     

Synthesis and properties of derivatives of symtriazine. 17. Synthesis of 2-methyl-4,6-disubstituted and 2,4-dimethyl-6-substituted sym-triazines by reduction of the corresponding trichloromethyl derivatives

The reduction of trichloromethyl groups in sym-triazine derivatives to methyl groups is studied. It is shown that 2-R-4, 6-bis (trichloromethyl)-sym-triazines can be reduced to 2-R-4, 6-dirnethyl-sym-triazines with zinc dust in ethanol or with lithium aluminum hydride in THF. 2-Amino, N-substituted 2-amino-, and 2-alkoxy-4-trichloromethyl-6-R-sym-triazines are reduced to the corresponding methyl derivatives by boiling with lithium aluminum hydride in dibutyl ether.I. M. Gubkin State Petroleum and Gas Academy, Moscow 117917. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 667–673, May, 1995. Original article submitted March 23, 1995.     

Synthesis of 1-O-acyl derivatives of carbohydrates through tert-butyl esters

Conclusions The synthesis of-D-glucopyranose pentaacetate,-maltose octaacetate, 1-O-benzoyl-2,3,4,6-tetra-O-acetyl--D-glucopyranose, and 1-O--(N-carbobenzoxy-L-alanyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose was accomplished by the reaction of acylhaloses with the tert-butyl esters of the corresponding acids.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1657–1658, July, 1972.     

Synthesis of substituted derivatives of imidazo [5, 1-b] benzimidazole

Heating, either molten or in high-boiling solvents, 1-methyl-2-[(N-phenylthiocarbamoyl)amino] (pyrid-4-yl)-methylbenzimidazole, or refluxing with phosphorus oxychloride in benzene acyl derivatives of 1-methyl-2-[(pyrid-4-yl)(amino)]- and 1-methyl-2 [(phenyl)(amino)]-methylbenzimidazoles, gives the corresponding derivatives of the imidazo [5, 1-b] benzimidazole system, hitherto undescribed in the literature.     

Conical for stepwise, glancing for concerted: the role of the excited-state topology in the three-body dissociation of sym-triazine

The highly debated three-body dissociation of sym-triazine to three HCN products has been investigated by translational spectroscopy and high-level ab initio calculations. Dissociation was induced by charge exchange between the sym-triazine radical cation and cesium. Calculated state energies and electronic couplings suggest that sym-triazine is produced in the 3s Rydberg and pi* <-- n manifolds. Analysis of the topology of these manifolds along with momentum correlation in the dissociation products suggest that the 3s Rydberg manifold characterized by a conical intersection of two potential energy surfaces leads to stepwise dissociation, while the pi* <-- n manifold consisting of a four-fold glancing intersection leads to a symmetric concerted reaction.     

Synthesis of thiophosphoryl-substituted derivatives of cycloalkanecarboxylic acids

The 1-thiophosphorylated esters and nitriles of cycloalkanecarboxylic acids were obtained both by the direct reaction of derivatives of thiophosphorylacetic acids with ,-dihalogenoalkanes in the K₂CO₃/DMSO heterophasic system, and as a result of the reaction of the corresponding oxygen compounds with the Louson reagent.A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, 117813 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 2, pp. 391–397, February, 1992.     

Synthesis of biphenyl derivatives by coupling reaction of halobenzenes with organonickel (0) complexes

A study of the coupling reaction of substituted halobenzenes with a zero valent pyridine-nickel complex as catalyst, leading to biphenyl derivatives, has been made. Electron-releasing groups as substituents favor the formation of coupling products in low yields, while electron-withdrawing groups as substituents suppress the formation of dimers.

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Synthesis of unsaturated diketones and δ2-pyrazoline derivatives from terephthalaldehyde

,-Unsaturated diketones were obtained by the condensation of terephthalaldehyde with aromatic and heterocyclic methyl ketones. The reaction of the diketones with phenyl-hydrazine gave 1,4-bis(1-phenyl-3-aryl-²-pyrazolin-5-yl)benzenes.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1096, August, 1971.     

Synthesis and properties of azoles and their derivatives. 10. Synthesis of 3,5-diaryl-4-nitroisoxazoles

A method was proposed for the synthesis of 3,5-diaryl-4-nitroisoxazoles entailing the brominatian of potassium salts of the corresponding 3,5-diaryl-²-isoxazolinyl-4-nitronic acids. The method may be used for the conversions of both the trans and cis isomers of 3,5-disubstituted 4-nitro-²-isoxazolines.Communication 9, See [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 189–192, February, 1985.