Synthesis of 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide

5-Amino-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide reacts with nitronium tetra-fluoroborate to give 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide. This compound is of interest as a new energetic material. A plausible reaction mechanism involves electrophilic substitution of the tert-butyl-NNO-azoxy group by the nitro group.

     

Synthesis of 2-alkyl(aryl,hetaryl)-4-methyl-1,2,3,4-tetrahydroquinolines

We have developed a preparative, three stage of synthesis of substituted 1,2,3,4-tetrahydroquinolines. Treatment of N-aryl-imines with allylmagnesium bormide gave N-aryl-N-alkenylamines which were cyclized to the tetrahydroquinolines. The configurations and conformations of the 4-methyl-1,2,3,4-tetra-hydroquinolines containing different 2- substituents have been determined.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 73–78, January, 1994.     

Synthesis of 7- and 5,7-substituted-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolines: Convenient precursors of quinolone antibacterial agents

An original procedure to obtain substitution at the 7 or 5, 7 positions on 6-halogenated tetrahydroquinaldines is described. The title products are a new class of precursors of quinolone antibacterial agents.     

Synthesis and some conversions of 6-methyl- and 1,6-dimethyl-5-nitro-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidines

Using a modification of the Biginelli reaction, we have synthesized 6-methyl- and 1,6-dimethyl-5-nitro-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidines. We have studied some of their chemical conversions involving the methyl group on the C₍₆₎ atom, the nitrogen atoms of the pyrimidine ring, and the phenyl substituent.Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 3, pp. 388–392, March, 1993.     

Synthesis of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,6-naphthyridines by a directed lithiation reaction

N-(tert-butoxycarbonyl)anilines (7), are easily converted in a one pot reaction sequence into the N- (tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolines (8), by directed ortho lithiation followed by reaction with 1- chloro-3-iodopropane, hence providing a new versatile quinoline ring nucleus synthesis. In an analogous reaction 2-N-(tert-butoxycarbonyl)- and an 2-N-(pivaloylamino) pyridine are converted to 1,2,3,4-tetrahydro-1,6- naphthyridines.     

Synthesis and structure of 2-aryl-2,4-dimethyl-1,2,3,4-tetrahydroquinolines and 1,3-disubstituted indenes

It has been shown that the intramolecular cyclization of N-(1-arylbutenyl)arylamines under acid catalysis conditions may proceed in two directions with the formation of 2-aryl-2,4-dimethyl-1,2,3,4-tetrahydroquinolines and 1,3 disubstituted indenes.     

Electronic absorption spectra of 2-amino-6-nitro-, 4-amino-3-bromo-and 5-amino-2-bromotoluenes

A new technique—photoacoustic spectroscopy—has been used for the first time to record the u.v.-vis spectra of three substituted toluenes, namely 2-amino-6-nitrotoluene, 4-amino-3-bromotoluene and 5-amino-2-bromotoluene. The π-π* electronic transitions analogous to the benzene first primary and secondary transitions could be detected from the PAS spectra in comparison with the u.v. solution and vapour spectra recorded by conventional methods. Detection of singlet → triplet absorptions from the PAS spectra, with significant intensity, is considered to be an important feature which transitions are in general either not observed or observed with only very weak intensity, in solution or vapour, by conventional methods. The analysis shows that a few excited state combinations observed in the u.v. PAS spectra of the molecules presently studied are well comparable with such combinations in ground state observed in the near i.r. PAS spectra.     

Synthesis of 2-amino-5-nitro-4H-pyran-3-carbonitriles

Reaction of 2-carbomethoxy-ω-nitroacetophenone with arylmethylenemalononitriles gives the previously unknown 2-amino-4-aryl-5-nitro-6-(2-carbomethoxyphenyl)-4H-pyran-3-carbonitriles. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. E-mail: muskat@cacr.ioc.ac.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1661–1663, December, 1998.     

Sulfuration of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinolines

Conclusions Substituted 2,2,4-trimethyl-1,2,3,4-tetrahydroquinolines upon reaction with a six-fold amount of sulfur at 210–220°C, similarly to dihydroquinolines, give the corresponding 4,5-dihydro-4,4-dimethyl-2,3-dithiolo[3,4-c]quinoline-1-thiones.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 191–192, January, 1989.     

Synthesis of 2-methyl-3-nitro-4-phenyl-1,4-dihydroquinoline

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, p. 1696, December, 1989.