Synthesis of 2,7-naphthyridines by the recyclization of trimethylformyl-piperidone

The structure of the product of interaction of the sodium salt of 1, 2, S-trimethyl-3 formylpiperid-4-one with cyanothioacetamide was specified. It was shown that the Knoevenagel adduct formed at the first stage in basic conditions undergoes recyclization with the formation of 1, 2,3,5,6, 7, 8, 8a-octahydro-l-oxo-6, 7, 8a-trimethyl-4-cyano-2, 7-naphthyridine-3-thione, the structure of which was confirmed by the data of physicochemical methods of analysis and chemical conversions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 512–515, April, 1996.     

Structure of the condensation product of benzalaniline with N,N-dimethylamide of dichloroacetic acid under darzens reaction conditions

Condensation of benzalaniline with N,N-dimethylamide of dichloroacetic acid under Darzens reaction conditions was used to obtain r-1, t-3-diphenyl-c-2-chloro-2-(NN-dimethylcarbamoyl)aziridine. The structure was established by x-ray diffraction analysis. Stabilization of the position of the substituents at the atoms of the aziridine ring by the hyperconjugation interaction of the unshared electron pair of the nitrogen atom with the antibonding orbital of the C-CI bond is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 189–192, February, 1994. Original article submitted November 30, 1993.     

Crystal and Molecular Structure of 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)resorcinol

The structure of 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)resorcinol in the crystal is virtually identical to that of 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)mesitylene, which is an effective antioxidant.     

Condensed tetrazolo-1,3,5-triazines. 4. Synthesis of salts of 5-aminotetrazolo[1,5-a]-1,3,5-triazin-7-one

2-Amino-4-azido-1,3,5-triazin-6(1H)-ones were synthesized by successive substitution of the trinitromethyl groups in 2-amino-4,6-bis(trinitromethyl)-1,3,5-triazines under the influence of azide and nitrite ions. Interaction of 2-amino-4-azido-1,3,5-triazin-6(1H)-ones with bases led to the azido-tetrazole tautomeric conversion give salts of 5-aminotetrazolo[1,5-a]-1,3,5-triazin-7-one. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1211–1219, August, 2006.     

Synthesis of new macrocyclic aminomethylphosphines based on 4,4"-diaminodiphenylmethane and its derivatives

The reaction of bis(hydroxymethyl)phenylphosphine with 4,4"-diaminodiphenylmethane in DMF afforded 1,1",5,5"-bis[methylenedi(p-phenylene)]di(3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane) (1) whose structure was established by X-ray diffraction analysis. Sulfurization and oxidation of macrocyclic tetraphosphine 1 gave rise to products 2 and 3, respectively, compound 3 being obtained as a stable hexahydrate. The reaction of bis(hydroxymethyl)phenylphosphine with bis(4-N-methylaminophenyl)methane in DMF followed by sulfurization yielded monocyclic bis{methylenedi[p-phenylene(N-methyl)aminomethyl]}di(P-phenyl)phosphine sulfide (4).     

Regio- and stereoselectivity of the reactions of pyridinium and picolinium salts and ylids with nitriles containing a nucleofugic group

The reaction of pyridinium, 2-picolinium, and 3-picolinium ylids with tetracyanoethylene, ethoxymethylenemalononitrile, and (dimethylthio)methyl-enecyanamide in the presence of organic bases proceeds regio- and stereo-selectively to give substituted pyridinium 1,4-ylids, 2-(2-propen-1-ylidene)-1,2-dihydropyridines, and 5-(1-pyridino)pyrimidin-4-olates, respectively. The reaction of 1-phenacylpyridinium bromide and tetracyanoethylene leads to 1-phenacylpyridinium tricyanoethenolate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 939–942 April, 1990.     

The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.0<Superscript>2,7</Superscript>]tridec-2-ene-13,4′-piperidine]

5,11-Disubstituted derivatives of 1′-isopropyl-8-thioxospiro[3,5,7,11-tetrazatricyclo[7.3.1.0^2,7]tridec-2-ene-13,4′-piperidine]-1,9-dicar bonitrile was obtained by the interaction of 10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,10-diene-8-thiolate with 2 equiv. of a primary amine and excess of formaldehyde. An anomalous reaction product was obtained with o-toluidine — 7,9-dicyano-1′-isopropyl-3-(2-methylphenyl)-1,2,3,4-tetrahydrospiro[pyrido[1,2-a][1,3,5]triazine-8,4′-piper idinium]-6-thiolate. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, 1709–1713, November, 2007.     

Reactions of α-Aminoalkylphosphonates with Iso(thio)cyanatophosphates(phosphonates,phosphinates). Synthesis of 1,3,4-Diazaphospholidines and 1,3,4-Oxaza(thiaza)phospholines

Phenyl -aminoalkylphosphonates add to phenyl iso(thio)cyanates to give saturated heterocycles, 1,3,4-diazaphospholidin-2-(thi)ones. The reaction of diphenyl (-methylamino)benzylphosphonate with diethyl isothiocyanatophosphate involves initial formation of 1,3,4-tiazaphospholidine-2-thiones containing exo- and endocyclic phosphorus atoms. These products are readily hydrolyzed in air, yielding diethyl isothio- cyanatophosphate and phenyl hydrogen (-methylamino)benzylphosphonate. The final products of the reaction of chloromethyl isocyanatophosphonates with aminoalkylphosphonates are 1,3,4-oxazaphospholines. Phenyl aminoalkylphosphonates react with chloromethyl isocyanatophosphonates to give saturated heterocycles, 1,3,4-diazaphospholidines, whereas with chloromethyl isothiocyanatophosphonates 1,3,4-thiazaphospholines are formed.     

The structure of 1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one

Crystal and molecular structure of 1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one as a product of the benzoylation of 1-phenyl-3-benzoylaminopyrazol-2-in-5-one was characterised by X-ray single crystal diffraction. It is shown that 1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one exists in the solid phase in an NH-tautomeric form, which is stabilised by two intramolecular hydrogen bonds and one intermolecular bond with the solvate dioxane molecule, the latter being used as a solvent for recrystallisation.