A new approach to the synthesis of 16-heteroprostanoids via isoxazole intermediates

Translated from Khimiya Geterotsiklicheskikh Soedinenii. Vol. 30. No. 3, pp. 424–425, March, 1994.     

Interaction of 4-aminobenzofurazan with aryldiazonium salts

The reaction of 4-aminobenzofurazan with aryldiazonium salts leads to the formation of 4-amino-5-aryl-azobenzofurazans and 5-amino-2-aryl-4-nitroso-2H-benzotriazoles, products of the rearrangement of the initially formed 4-amino-7-(arylazo)benzofurazans. Oxidation of the benzofurazan as well as of the triazole derivatives gives 7-aryl-1,2,3-triazol[4,5-e]benzofurazans. The chemical properties of some of the compounds obtained have been investigated.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1432–1438, October, 1994. Original article submitted July 25, 1994.     

Donor-acceptor complexes of quinoline N-oxides with boron trifluoride

Molecular n-v complexes of quinoline N-oxides with BF₃ have been studied by electronic and IR spectroscopy. In most case the donor centre is the oxygen atom of the N-oxide group.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1087–1092, August, 1994.     

Rearragnement of 1-allyloxy-2-allylthio-4-methyl-benzene TO 2,4-dimethyl-6-allyl-7 hydroxy-2,3-dihydrobenzothiophene

1-Allyloxy-2-allylthio-4-methylbenzene rearranges in NN-diethylaniline at 215°C with migration of allyloxy and allylthio groups to form 2,4-dimethyl-6-allyl-7-hydroxy-2,3dihydrobenzothiophene.M. V. Lomonosov State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 480–482, 1994. Original article submitted March 5, 1994.     

Use of ultrasound in heterocyclic chemistry (review)

We review literature data on synthesis and conversions of heterocyclic compounds using ultrasonic treatment.We analyze the effect of ultrasound on organic reactions involving participation of heterocyclic compounds.A. N. Kosygin State Technical Academy, Moscow 117918. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–755, June 1994. Original article submitted December 22, 1993.     

Synthesis,structure, and chemical properties of some N-(3-chloro-2-quinoxalyl)arylsulfonamides

We have developed a method for synthesis of N-(3-clzloro-2-quinoxalyl)sulfonamides by reaction of 2,3-dichloroquinoxaline with substituted arylsufonamides. Based on the IR spectra, we have established that in the solid state, the synthesized compounds exist in the form of amide tautomers. Alkylation of these compounds leads to N-metliyl-N-(3-chloro-2-quinoxalyl)arylsulfonamides. We demonstrate the possibility of nucleophilic substitution of the halogen upon treatment with O- and N-nucleophiles. The use of bifunctional nucleophiles leads to condensed quinoxalines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 30, No. 3, pp. 387–392, March, 1994.     

Synthesis and ring-chain isomerism of acid chlorides and amides of 2-(2-pyridyl and 2-quinolylcarbonyl) benzoic acids

The reaction of 2-(2 pyridytcarbonyl)benzoic acid with thionyl chloride affords an unexpected product of the intramolecular acylation of the pyridine nitrogen atom, namely, 6,11-dioxo-6,11-dihydrobenzo[blquinotizinium chloride. At the same time, 2-(2-quinotylcarbonyl)benzoic acid forms the expected cyclic acid chloride, namely, 3-(2-gitinotyl)-3-chlorophthalide in this reaction. Both compounds acylate ammonia and primary amines, including those with bulky alkyl groups (tert-butyl, 1-adamantyl, and 1,1,3,3-tetramethylbutyl) with the formation of 2-R-3-hydroxy-3-(2pyridyl- or 2-quinolyl)isoindolines. The protonation of the pyridine nitrogen atom of N-(1,1,3,3-tetramethylbutyl)-2-(2pyridylcarbonyl)benzamide, obtained in the open amide form, is accompanied by the closing of the isoindotinone ring; the deprotonation is accompanied by ring opening.Riga Technical University, Riga LV-1048. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 499–504, April, 1994. Original article submitted March 17, 1994.     

Aziridinylketones and their cyclic anils. 12

We have measured the PMR spectra of 5, 7-diaryl-1, 4-diazabicyclo[4. ].O]hept-4-enes. We have studied the structure of the 5-(4-nitrophenyl)-7-phenyl derivative by x-ray diffraction. We show that the six-membered heterocycle has the half-chair form. The 6-H and 7-H protons of the aziridine ring are trans, while the 7-aryl is exo relative to the six-membered ring. Introduction of substituents into the aromatic ring has practically no effect on the geometry of the bicycle.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1117–1124, August, 1994.For Communication 11, see [1].