Synthesis of halogenoazoles

On reaction with halogens, organolithium and organomagnesium derivatives of azoles are converted into halogenoazoles. Halogen derivatives of N-substituted imidazoles, benzimidazoles, and indazoles have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1109–1111, August, 1973.     

Organolithium and organosodium compounds of n-substituted 2-alkylbenzimidazoles

Organolithium and organosodium compounds of 1,2-dimethyl-, 1-methyl-2-ethyl-, 1-methyl-2-propyl-, and 1-phenyl-2-methylbenzimidazole, containing the metal in the alkyl group at position C(₂), were obtained by metallation. It was found that metallation can be complicated by the addition of the metalling reagent at the C=N bond of the heterocycle. It was shown that the obtained organometallic compounds can be used for the synthesis of various derivatives of benzimidazole.The calculation was performed with the standard bond lengths. A planar model was used for the carbanion.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1073–1077, August, 1986.     

Synthesis and reactions of 4-(benzothiazol-2-yl)-2,6-dimethylpyrylium perchlorate

A new method has been developed for the synthesis of 4-(benzothiazol-2-yl)-2,6-dimethylpyrylium perchlorate from 2,6-dimethyl--pyrone and 2-lithiobenzothiazole. The reaction of this salt with ammonia and with primary and secondary amines, hydrazine, phenylhydrazine. and hydroxylamine leads to the formation of difficultly accessible hetaryl-substituted benzothiazoles.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1016–1019, August, 1973.     

Synthesis and nonchair conformations of 2,2-disubstituted 4,4-dimethyl-1, 3-dioxanes

The fundamental possibility of the synthesis of 2-substituted 1,3-dioxanes by reaction of 1,3-dioxanium perchlorates with organometallic compounds is demonstrated. A method for the synthesis of acyl derivatives of heterocycles was developed on the basis of these compounds. The existence of 2,2,4,4-substituted 1,3-dioxanes in the twist conformation was shown by ¹H NMR spectroscopy; the twist conformation is explained by the effect of nonbonded 1,3-syn-axial interactions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1172–1179, September, 1978.