Synthesis and some transformations of 4-aryl-substituted amines of the tetrahydropyran series

The reaction of 2-isopropyltetrahydropyran-4-one [obtained by isomerization and hydration of 3-isopropylpent-1-en-4-yn-3-ol in the presence of 5% sulfuric acid and mercury(II) sulfate] with ethyl cyanoacetate gave ethyl cyano(2-isopropyltetrahydropyran-4-ylidene)acetate which was treated with 4-tolylmagnesium chloride. The resulting ethyl cyano[2-isopropyl-4-(4-tolyl)tetrahydropyran-4-yl]acetate was subjected to decarbethoxylation to obtain 2-isopropyl-4-(4-tolyl)tetrahydropyran-4-ylacetonitrile. The latter was reduced to the corresponding amine with lithium tetrahydridoaluminate, and the reduction product was brought into condensation with aromatic aldehydes. The Schiff bases thus formed were reduced with sodium tetrahydridoborate, followed by N-acylation with acetyl and propionyl chlorides.     

Novel transformations in the quassin series

A series of remarkable rearrangement reactions involving (1β,9β)-1-methoxypicras-11-en-16-one and related derivatives are described.     

Some transformations of dimethylaminovinylpyrimidines

The reaction of enamines of the pyrimidine series with phenyl isothiocyanate, arenediazonium salts, and benzylamine was studied. The corresponding thioamides, pyrimidinylacetaldehydes, and benzylaminovinylpyrimidine were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 559–561, April, 1985.     

Some transformations of N-aminomethylisatins

N-Aminomethylisatins readily split out an aminomethyl residue; they condense with acetone to give N-aminomethyl-3-acetonyldioxindoles and with indole to give N-aminomethyl-3-(3-indolyl)dioxindoles, which readily split out an aminomethyl residue.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1211–1214, September, 1976.     

Some transformations of fluorochloronitroalcohols

Conclusions Previously unreported bis(fluorochloronitroalkyl) sulfites were obtained upon carrying out the reactions with flushing of hydrogen chloride by an inert gas or using an amine acceptor, while the reaction with SOCl₂+DMF (the Weismeier-Haake reagent) gives O-formylation. Fluorochloronitromethyl ketones were obtained for the first time upon the oxidation of secondary fluorochloronitroalcohols using potassium dichromate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1423–1426, June, 1989.     

Synthesis of amines of the di-and trifurylmethane series

Methods are proposed for the synthesis of amines of the di-and trifurylmethane series-prospective compounds for the production of polymers and macrocyclic molecules-on the basis of 2-(2-furylmethyl)-1,3-isoindolinedione. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 505–512, April, 2007.     

Deamination of amines of adamantane series

Conclusions The deamination of 1-aminoadamantane, 1,3-diammoadamantane and 1-amino-3-adamantanol leads to the formation of the corresponding alcohols. The isomerization of the adamantane skeleton was not observed in all cases.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimlcheskaya, No. 10, pp. 2378–2379, October, 1973.     

Sigma complexes in the pyrimidine series. 3. Some transformations of anionic sigma complexes of 5-nitropyrimidines

It is shown that sigma complexes of 5-nitropyrimidines with acetonide are protonated at the ring nitrogen atom in acidic media to give 5-nitroacetonyldihydropyrimidines. The latter are oxidized by dichlorodicyanobenzoquinone to 5-nitroacetonylpyrimidines.See [1] for Communication 2.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 823–826, June, 1981.     

Synthesis of amines of the tetrahydro-3-furyl series

From ß-tetrachlorotetrahydrofuran a series of aromatic and aliphatic amines has been synthesized, the members of which are of interest as biologically active compounds. It is shown to be possible to convert them to water-soluble salts by sequential treatment with chloroacetyl chloride and pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 309–311, March, 1994.     

Synthesis and transformations of acids of the triazole series

3,5-Di(m- and p-tolyl)-1,2,4-triazples were obtained by reaction of formalin with 2,5-ditolyl-1,3,4-oxadiazoles and subsequent hydrolysis of the resulting formyl derivatives. 3,5-Di(o-tolyl)-1,2,4-triazole cannot be obtained by this method. The oxidation of 3,5-ditolyl-1,2,4-triazoles leads to 3,5-bis(carboxyphenyl)-1,2,4-triazoles, which were converted to diesters and dihydrazides.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 848–849, June, 1978.     

Semi-empirical calculations of dihydropyran conformations

Semi-empirical calculations of dihydropyran conformations have been performed using a Karplus-type equation with the sum of chemical shifts as a correction parameter. A graphical method has been proposed to evaluate the conformational state of the molecules.     

Acetylenic alcohols and amines of the diphenyl oxide series

Conclusions A number of alcohols and amines-derivatives of 4-ethynyldiphenyl oxide and 4,4 -diethynyldi-phenyl oxide-were synthesized. Important differences in the reactivity of the starting mono- and diacetylenes in the Favorskii and Mannich reactions were not detected.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 905–908, April, 1967.