Synthesis and some transformations of dimethyl anabasylethynephosphonate

A new phosphorylated ynamine, dimethyl anabasylethynephosphonate, was synthesized by reaction of dimethyl chloroacetylenephosphonate with anabasine. Anabasylethynephosphonate obtained was shown to react under mild conditions with primary aromatic amines like p-chloroaniline, p-anisidine, and p-aminoacetophenone, whose pK _b values are in the range of 9–13, to form new asymmetrical phosphorylated acetamidines in high yields. Structure of the compounds obtained was proved by ¹H, ¹³C, and ³¹P NMR spectroscopy.     

Reactions of silyl nitronates with dimethylformamide dimethyl acetal as a new general procedure for the synthesis of 2-nitroenamines

Silyl nitronates obtained in situ from the corresponding aliphatic nitro compounds react with dimethylformamide dimethyl acetal giving 2-nitroenamines in moderate to good yields. The reaction pathway is discussed.     

Stereochemical transformations of some seven-membered pyridoxine dimethyl ketals

According to the data of single crystal X-ray diffraction analysis and computational methods, the seven-membered rings of acylated pyridoxine acetonides have C ₂ symmetry. Two stereochemical transformations in solutions, enantiotopomerization of P-, M-conformations with spiral chirality of twist-boat forms and diastereotopomerization of structures that differ in the configuration of the phenolic oxygen substituents, were revealed by dynamic ¹H NMR spectroscopy.     

Reaction of some heterocyclic ketones with lithium dimethyl copper

Reaction of lithium dimethyl copper with several heterocyclic ketones results in a 1,4-addition and introduction of a methyl group on the heterocyclic ring. In some cases, addition to the carbonyl also occurs.     

Reaction of octafluoroisobutene with dimethylformamide

Conclusions Octafluoroisobutene reactsundermild conditions with dimethylformamide with formation of 3,3,3-trifluoro-N,N-dimethyl-2-(trifIuoromethyl) propenylamine and perfluoropivaloyl fluoride.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 346–351, February, 1967.     

Methods for controlling the regioselection in the reaction of 3-amino-5-benzylthio-1,2,4-triazole with acetylacetaldehyde dimethyl acetal

The reaction of 3-amino-5-benzylthio-1,2,4-triazole with acetylacetaldehyde dimethyl acetal affords 2-benzylthio-5-methyl-1,2,4-triazolo[1,5a]pyrimidine or 2-benzylthio-7-methyl-1,2,4-triazolo[1,5a]pyrimidine regioselectively depending on the reaction conditions.     

Reaction of aminoquinolines with methyl acrylate and transformations of some of the products obtained

3H,4H-Quino[1,2-a]-2-pyrimidone, 1-(2-carboxyethyl)aminoquinolinium betaines, and methyl esters of N-quinolinyl--alanines were isolated from the reactions of aminoquinolines with methyl acrylate. Hydrolysis of the latter yielded the corresponding amino acids, two of which were converted to 1-(3- and 6-quinolinyl)dihydrouracils, and the latter was reduced to 1-(6-quinolinyl)-2-oxohexahydropyrimidine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 482–486, April, 1971.     

Structure of the product of the reaction of the dimethyl sulfide-sulfur trioxide complex with methylenecyclobutane

L. Ya. Karpov Scientific-Research Institute of Physical Chemistry. Translated from Zhurnal Strukturnoi Khimii, Vol. 32, No. 3, pp. 111–113, May–June, 1991.     

Reaction of epoxybutyraldehyde diethyl acetal with ammonia and benzylamine

Conclusions The opening of the oxide ring of the diethyl acetal of epoxybutyraldehyde by ammonia or benzylamine goes selectively both structurally and sterically, with the formation of o-hydroxy--amino compounds of the erythro series.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 919–920, May, 1966.     

Acetals of lactams and acid amides 55. Study of reaction of 3-oxopyridine and isoquinolin-3-one derivatives with dimethylformamide diethyl acetal

The reactions of 4-carbamoyl- and 4-cyanopyridin-3-one and 4-cyanoisoquinolin-3-one with DMFA diethyl acetal were studied, and hydrogenated di- and trimethylene derivatives of 2,7-naphthyridine-1,8-dione were synthesized. It was found that O- or N-alkylation reactions of the pyridone fragment of the starting bicyclic compounds take place together with the condensation of the DMFA acetal at the amide amino group or the active methylene unit.For Communication 54, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 215–220, February, 1990.     

Reaction of 3-azido-5-phenyl-1,2,4-oxadiazole with dimethylformamide,a new deoxygenative coupling reaction

When 3-bromo-5-phenyl-1,2,4-oxadiazole (1b) is heated with sodium azide in anhydrous dimethylformamide at 130°, 3-dimethylamino-($\text{1c}$) and 3-dimethylaminomethyleneamino-5-phenyl-1,2,4-oxadiazole ($\text{1d}$) are formed, the latter by a new deoxygenative coupling of the azide ($\text{1a}$), or the nitrene derived from it, with the solvent.