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.     

Hydroxyl-containing mesogens. Synthesis and liquid-crystalline properties of 2-o-hydroxyarylpyrimidines

We have synthesized 5-alkyl(alkoxy)-2-(o-lzydroxy-p-alkoxyphenyl)pyrimidines and considered the effect of the OH group on the inesomorphism. We have found that in binuclear o-hydroxyarylpyrimidines, an ortho OH group forming an intramolecular hydrogen bond increases T_mp, inhibits the appearance of nematic properties, and promotes the appearance of a smectic A.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 30, No. 1, pp. 90–92, January, 1994.     

Synthetic analogs of natural flavolignans. V. A new synthesis of 6-halogeno-1,3-benzodioxane analogs of silandrin and hydnocarpin

6-Halogeno-1,3-benzodioxane analogs of chalcones have been synthesized by various methods. Flavanone and flavone analogs of silandrin and hydnocarpin have been obtained from them. The structures of the new flavonoids have been shown by their PMR spectra.     

Luteolin glucosides fromFerula varia

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 891475. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 679–680, September–October, 1994.     

Essential oil ofChaerophyllum macrospermum

Institute of Botany, Academy of Sciences of the Republic of Azerbaidzhan, Baku. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 291–292, March–April, 1994.