Simple method for the preparation of 1-oxo-1-chlorophospholenes

Conclusions A new and simple method has been found for the synthesis of 1-oxo-1-chlorophospholenes by the reaction of phosphorus trichloride, a diene, and an oxygen-donor compound, the best of which is acetone.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1847–1848, August, 1972.     

Ring contraction of 1,3-bis(5-bromopentyl)alloxazine

The reaction of 1,3-bis(5-bromopentyl)alloxazine with ethylamine in propan-2-ol resulted in replacement of the terminal bromine atoms by ethylamino groups and was accompanied by contraction of the pyrimidine ring so that the products were 1,3-bis[5-(ethylamino)pentyl]alloxazine and 1,3-bis[5-(ethylamino)-pentyl]imidazo[4,5-b]quinoxalin-2-one.     

Synthesis and properties of N-[ω-(p-toluenesulfonoxyl)alkyl]uracils

Conclusions The possibility of N-(-hydroxyalkyl)uracil tosylates undergoing intramolecular cyclization to give bicyclic pyrimidinium salts was studied.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2349–2356, October, 1980.     

Isomerization of 1-oxo-1-chlorophospholenes in the presence of phosphorus trichloride

The isomerizing action of phosphorus trichloride on phospholene derivatives was observed. It was shown that mixtures of isomers, with predominance of 2-phospholene, are formed when isomerically pure 1-oxo-1-chlorophospholenes are heated in the presence of phosphorus trichloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1616–1619, December, 1971.     

Synthesis of pyrimidinophanes containing nitrogen atoms in polymethylene bridges

The reactions of 1,3-bis(-bromobutyl- or -pentyl)-6-methyluracil with 1,3-bis(-ethylaminobutyl- or -pentyl)-6-methyluracil afforded pyrimidinophanes containing N atoms in bridging polymethylene chains. Individual geometric isomers of pyrimidinophanes were isolated. The structure of one of these isomers was established by X-ray diffraction analysis. Quaternization of the bridging N atoms with o-nitrobenzyl bromide gave rise to water-soluble pyrimidinophanes.     

Synthesis,IR Spectra,and Steric Structure of Macrocycles Derived from Pyrimidine Compounds

A new macrocycle including pyrimidine fragments, 12,23,36-trimethyl-24,40-dioxo-15,33-dithia-2,9,13,22,26,35,38,39-octaazatetracyclo[32.3.1.110,14.122,26]tetraconta-1(38),10(39),11,13,23,34,36-heptaene, was synthesized. According to the data of IR and UV spectroscopy and HF/6-31G** quantum-chemical calculations, macrocyclic compounds of this series in crystal exist in the amino form, one NH group of which is likely to be involved in intramolecular hydrogen bond, and the other, in intermolacular hydrogen bond. The strength of the latter depends on the macroring size. In solution, the above structures are supplemented by conformers containing both intramolecularly H-bonded and free amino groups, predominantly with trans structure of the HÄNÄCÍN fragment. The imino form of the aminopyrimidine moieties is hardly probable.     

Regulation of the rate of hydrolysis of phosphorus acid esters in organized systems based on amphiphilic pyrimidinophanes

The aggregation and catalytic activity of supramolecular systems based on new macrocyclic dimeric surfactants (pyrimidinophanes) was studied both in the absence and in the presence of polyethyleneimine (PEI). It was found that the critical micelle concentrations measured by tensiometry were independent of the structure of surfactants. The morphology of aggregates was responsible for various characters of the catalytic effects of pyrimidinophanes in the hydrolysis of phosphonic acid esters. A less hydrophobic pyrimidinophane exhibited a typical effect of cationic surfactants to accelerate the reaction both in the absence and in the presence of PEI. Unlike cationic micelles, a heminal-type pyrimidinophane exhibited an anomalous behavior: it had no effect on the rates of hydrolysis of the substrates and did not inhibit the hydrolysis. Upon the addition of lanthanum ions, the catalytic activity of dimeric surfactants increased. The overall catalytic effect due to the action of supramolecular systems based on pyrimidinophanes, PEI, and lanthanum ions can increase the rates of hydrolysis of the substrates by three orders of magnitude, as compared with that of alkaline hydrolysis.     

Heterocyclophanes with 6-methyluracyl and hydantoin fragments. Ring contraction in 1,3-bis(5-bromopentyl)-5-nitrouracyl

Russian Journal of Organic Chemistry -     

Reaction products of selenophosphorus acid esters with sulfuryl chloride

Conclusions Selenophosphorus acid esters react with SO₂Cl₂ to form -chlorose lenophosphonium salts, while reaction of O,O-dialkyl selenophosphoric acids with SO₂Cl₂ under analogous conditions gives O,O-dialkyl Se-chloro selenophosphates.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khi miche ska ya, No. 1, pp. 153–156, January, 1977.