Synthesis of pyridine bases from piperidine derivatives

The corresponding substituted pyridines are obtained in 40–90% yields when N-alkyl-substituted piperidines, gD⁴-piperideines, and secondary and tertiary -piperidols are heated at 240–270C with pyridine N-oxide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 787–789, June, 1977.     

1,3-diphenyl-2-azaanthracene and 8-aza-7-phenylbenzo[a]fluoranthene in the diene synthesis

The diene condensation of 1,3-diphenyl-2-azaanthracene with maleic anhydride proceeds under more severe conditions than the analogous condensation with anthracene. On the basis of an analysis of the PMR data for the adduct obtained it was assumed that isomers of ,-[9,10-dihydro-2-aza-1,3-diphenylanthrylene(9,10)]succinic anhydride with respect to the position of the anhydride bridge relative to the pyridine ring are formed in this condensation. 9,10-Dihydro-2-aza-1,3-diphenyl-9, 10-(1-cyanoethylene)anthracene was obtained in the condensation of the same azaanthracene with acrylonitrile. ,-[5H-8-Aza-7-phenylbenzo[a]fluoranthrylene (5,12b) ]succinic anhydride is formed as a result of the similar condensation of 8-aza-7-phenylbenzo[a]fluoranthene with maleic anhydride, while isomeric (with respect to the position of the nitrile group in the ethylene bridge) 5H-8-aza-7-phenyl-5,12b-(cyanoethylene)benzo[a]fluoranthenes were isolated in its condensation with the acrylonitrile. Data from the PMR and IR spectra were used to prove the structures of the adducts of the diene synthesis obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1645–1647, December, 1980.     

Synthesis of hexahydroazonino[5,6-b]indoles from hexahydroazepino[4,3-b]-and-[3,4-b]indoles and activated alkynes

A reaction of substituted hexahydroazepino[4,3-b]-and-[3,4-b]indoles with activated alkynes was studied. A one-step method for the synthesis of isomeric hexahydroazonino[5,6-b]indoles different by positions of the double bond in the azonine ring was developed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2244–2250, November, 2007.     

Structure of “furfuramide” and “furfurine”

The structures of ,-bis(furfurylideneimino)silvan (furfuramide or N,N'-difurfurylidene-2-furanmethanediamine) and the product of its thermal cyclization 2,4,5-tris (-furyl)-2-imidazoline (furfurine) were confirmed by comparison of the IR, UV, ¹H and ¹³C NMR, and mass spectra. It is shown that acetylation of the latter with acetic anhydride in the case of heating of the reagents without a solvent or in pyridine takes place with opening of the imidazoline ring and leads to the formation of 1,2-bis(-furyl)-1-acetamido-2-(-furoylamido)ethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1461–1464, November, 1978.     

N-oxides of 2- and 4-azafluorenones and nitro derivatives of 2- and 4-azafluorenes

It was demonstrated by PMR spectroscopy that mixtures of N-oxides of 6- and 7-nitro derivatives are formed in the nitration of the N-oxides of 3-methyl-2- and 4-azafluorenes. The products were deoxygenated to give nitro derivatives of 2- and 4-azafluorenes. The N-oxides of nitro-substituted azafluorenes were converted to salts of the aci forms by the action of alkali.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1396–1399, October, 1982.The authors thank K. F. Turchin for his assistance in recording the spectrum of nitration product VI at 200 MHz.     

Chemical reactions of 4,5,6,7-tetrahydro-4,5,7-trimethylpyrrolo[3,2-c]pyridine and its 2-formyl derivative

N-Alkyl substituted tetrahydropyrrolo[3,2-c]pyridines have been obtained by alkylation of 4,5,6,7-tetrahydro-4,-5, 7-trimethylpyrrolo[3,2-c]pyridine and its 2-formyl derivative chloroalkyldimethylamines, acrylonitrile, methyl acetylenedicarboxylate and dichloroethane. 2-Formyl substituted tetrahydropyrrolo[3,2-c]pyridine has been reduced with sodium borohydride and condensed with monoethanolamine and hydroxylamine. The stereochemistry of the products has been studied by ¹H NMR spectroscopy.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 681–687, May, 1993.     

Catalytic effect of aliphatic amine on the reaction of quinone diimine with 2-mercaptobenzothiazole

Russian Chemical Bulletin - A secondary aliphatic amine, N-benzylmethylamine, significantly increases the rate of the chain reaction of N,N′-diphenyl-1,4-benzoquinone diimine with...     

Catalytic effect of hydroxyl-containing compounds at the propagation step of the chain reaction of thiophenol with quinone imines

Russian Chemical Bulletin - Hydroxyl-containing compounds (water, methanol, and phenol) act as efficient catalysts of the chain reactions of thiophenol with quinone imines at their propagation...