4-(5-Arylvinyl-2-oxazolyl)- and 4-(5-arylbutadienyl-2-oxazolyl)-naphthalic anhydrides

4-(5-Arylvinyl-2-oxazolyl)- and 4-(5-arylbutadienyl-2-oxazolyl)naphthalic anhydrides were synthesized by a phosphonate modification of the Wittig reaction from 4-(5-bromomethyl-2-oxazolyl)naphthalic anhydride. The structures of the aryl radicals and the steric hindrance created by some of them have a substantial effect on the absorption and luminescence of these compounds in solution. The introduction of each of the vinylene groups between the aryl and heterocyclic radicals causes approximately identical shifts in the spectra, but the Stokesian shift increases. These effects are reinforced considerably under the influence of electron-donor substituents in the aryl radical. The luminescence maxima of the investigated substances range from 515 to 710 nm, and the absolute quantum yields range from 0.12 to 0.51.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 611–613, May, 1977.     

4-(5-aryl-2-oxazolyl)phthalic anhydrides

4-(5-Aryl-2-oxazolyl)-substituted phthalic anhydrides were synthesized from 4-chloroformylphthalic anhydride and various -aminomethyl aryl ketones. The spectral-luminescence properties of solutions of the products in toluene and 5% NaOH solution were investigated. It is shown that the introduction of substituents with different electronic natures in the 5-phenyl ring of 4-(5-phenyl-2-oxazolyl) phthalic anhydride has a significant effect on the spectral-luminescence characteristics of the synthesized compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 35–37, January, 1979.     

2-(5-甲基-2-苯基-噁唑基)乙醇的合成

2-(5-甲基-2-苯基-噁唑基)乙醇的合成;Dakin-West反应;还原     

Synthesis and study of the luminescence properties of anhydrides and n-phenylimides of 4-(2-aryl-1,3,4-oxadiazol-5-yl)naphthalic acids

4-(2-Aryl-1,3,4-oxadiazol-5-yl)naphthalic anhydrides were obtained by condensation of 4-chlorocarbonylnaphthalic anhydride with monohydrazides of substituted benzoic acids and subsequent cyclodehydration; the corresponding N-phenylimides were obtained from the 4-(2-aryl-1,3,4-oxadiazol-5-yl)naphthalic anhydrides. The UV and luminescence spectra are presented.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 461–463 April, 1974.     

Anhydrides and phenylimides of 4-(5-aryl-2-oxazolyl)naphthalic acids

A number of 4-(5-aryl-2-oxazolyl)naphthalic anhydrides were obtained by condensation of 4-chloroformylnaphthalic anhydride with -aminomethyl aryl ketones and subsequent cyclization of the resulting amides; N-phenylimides were obtained from the anhydrides by reaction with aniline. The relationship between the structures of the substances obtained and their UV and luminescence spectra was investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1331–1333, October, 1973.     

Synthesis and luminescence properties of 4-(2-methyl-5-oxazolyl)naphthalic anhydride and the products of its condensation with aromatic amines

4-(2-Methyl-5-oxazolyl)naphthalic anhydridewas synthesized by heating -aminomethyl 5-acenaphthyl ketone hydrochloride with acetic anhydride and subsequent oxidation of the resulting 2-methy1-5-(5-acenaphthyl)oxazole. 4-(2-Methyl-5-oxazolyl)-naphthalic acid phenylimide and 4(3)-(2-methyl-5-oxazolyl)-7-oxo-7H-benzimidazo-[1,2-b]benzo[de]isoquinoline were obtained by condensation of 4-(2-methy1-5-oxazo-lyl)naphthalic anhydride with aniline and o-phenylenediamine. The coincidence of the directions of polarization of the C=N bond of the oxazole ring and the electronic shifts in the system of the anhydride and phenylimide molecules leads to an increase in the quantum luminescence yield.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1613–1615, December, 1977.     

Synthesis of derivatives of α-phenyldinicotinic acid and 2-phenyl-3,5-bis(5-phenyl-2-oxazolyl)-pyridine

The dichloride, diethylamide, and amide were obtained from -phenyldinicotinic acid. 2-Phenyl-3,5-diamino- and 3,5-dicyanopyridine were synthesized from the amide. 2-Phenyl-3,5-bis(5-phenyl-2-oxazolyl)pyridine and 2-phenyl-3-carboxy-5-(5-phenyl-2-oxazolyl)pyridine were obtained. The luminescence properties of the synthesized compounds were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 405–411, March, 1990.The authors thank A. A. Ustenko and E. N. Smirnova for their assistance in calculation of the spectral data.     

Synthesis,structure, and spectral fluorescence properties of 1,4-di(5-phenyl-2-oxazolyl)benzene heteroanalogs

Novel organic luminophors belonging to the oxazole and oxadiazole classes of compounds have been synthesized, namely, thiophene and furan analogs of 1,4-di(5-phenyl-2-oxazolyl)benzene. The optical properties of these compunds have been studied both theoretically and experimentally. Their IR spectra have been measured and their UV absorption, fluorescence, and excitation spectra have been analyzed. Details of their electronic structure and their principal spectral fluorescence parameters have been calculated using the PPP method. Possible methods or pathways for improving the spectral fluorescence parameters of organic luminophors in these classes of compounds in the visible region of the spectrum have also been analyzed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1414–1419, October, 1989.     

Synthesis and properties of 1-methyl-2-phenyl-5-(2-furyl)- and 1-methyl-2-phenyl-5-(2-thienyl)imidazoles

2-Phenyl-5-(2-furyl)- and 2-phenyl-5-(2-thienyl)imidazoles were synthesized by condensation of 2-furoylmethyl and 2-thenoylmethyl acetates with benzaldehyde under the conditions of Weidenhagen reaction. The products were converted to N-methyl derivatives in the KOH-acetone system. The electrophilic substitution reactions of the products (acylation, bromination, nitration, sulfonation, hydroxymethylation) were studied.     

微波辐射下合成2-(未)取代苯甲酰胺基-5-(1-苯基-3-甲基-5-氯吡唑- 4-基)-1,3,4-噻二唑衍生物

分别在微波辐射和常规加热条件下, 通过2-氨基-5-(1-苯基-3-甲基-5-氯吡唑-4-基)-1,3,4-噻二唑(1)与(未)取代苯甲酰氯(2a～2j)反应, 合成了一系列未见文献报道的2-(未)取代苯甲酰胺基-5-(1-苯基-3-甲基-5-氯吡唑-4-基)-1,3,4-噻二唑衍生物(3a～3j). 标题化合物的结构经元素分析, IR, 1H NMR确证.     

Crystal structure and luminescence properties of 4-(4-benzoyloxy-2-hydroxyphenyl)-2,2-difluoro-6-phenyl-1,3,2-dioxaborine

The crystal structure of 4-(4-benzoyloxy-2-hydroxyphenyl)-2,2-difluoro-6-phenyl-1,3,2-dioxaborine (1) was determined by X-ray diffraction analysis. π-π-Stacking interaction between the molecules results in joining the molecules into a three-dimensional layered framework. Luminescence of the aggregates is observed in concentrated solutions of compound 1. Two routes of excimer formation in crystal were revealed by steady-state and time-resolved luminescence spectroscopy: via excitation of single molecules and via excitation of aggregates.     

Synthesis and liquid crystal properties of substituted 5-(arylcarbonyloxy)-2(p-cyanophenyl)pyrimidines

Liquid crystal p-substituted benzoates, biphenylcarboxylates, and benzoyloxybenzoates were obtained on the basis of 5-hydroxy-2-(p-cyanophenyl)pyrimidine. The development of nematogenicity by the esters due to the p-cyanophenyl grouping was noted, and the appearance of the smectic mesophase by the variation of the ring framework of the acid fragment of the molecule was investigated.Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (RAN), Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 371–376, March, 1995. Original article submitted December 19, 1994.     

Synthesis and photophysical studies of novel 4-aryl substituted 2-phenyl-, 2-(fluoren-2-yl)- and 2-cymantrenylquinazolines

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Antimicrobial activity of 3-(substituted methyl)-2-phenyl-4H-l-benzothiopyran-4-ones

A series of 3-(substituted Methyl)-2-phenyl-4H-l-benzothiopyran-4-ones (thioflavones) and thioflavone 1,1-dioxides was prepared to test for antimicrobial activity and for antitumor activity. It was shown that an introduction of a substituted methyl group in the 3-position of thioflavone resulted in significant antimicrobial activity against Trichophytons. 3-(Acetoxymethyl)thioflavone shows the most antimicrobial potency in vitro against Trichophyton mentagrophytes. Most of the thioflavone 1,1-dioxides showed antimicrobial activity against fungi. Five of the 40 related compounds demonstrated weak antitumor activity against P-388 lymphocytic leukemia.     

Synthesis and IR spectra of 5-phenyl-2-(1-phenyl-2-trichloroacetylethenyl)pyrrole

5-Phenyl-2-(1-phenyl-2-trichloroacetylethenyl)pyrrole was synthesized by the reaction of 2-phenylpyrrole with 1-phenyl-2-trichloroacetylacetylene on silicon oxide. The structure of an intramolecular proton-transfer H-complex was assigned to the title compound based on analysis of its IR spectra in solutions in the temperature range of 165–298 K. Published inIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 1945–1947, November, 2000.     

Synthesis starting from 3-methyl-2-phenyl-5-(3-methyl-2-phenyl-3,4-dehydropiperidyl-6)pyridine. 2-phenyldinicotinic and 4-azafluorenone-2-carboxylic acids

N-Methyl (ethyl, benzoyl, trifluoroacetyl)-substituted 3-methyl-2-phenyl-5-(3-methyl-2-phenyl-3,4-dehydropiperidyl-6) pyridines and di(N-oxide) of the correspondingly substituted ,ß-dipyridyl were prepared. A method for synthesizing 2-phenyldinicotinic acid was developed. Cyclodehydration of this acid gave 4-azafluorenone-2-carboxylic acid. Transformations of this acid were carried out with respect to two functional groups.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 813–817, June, 1986.     

Synthesis and spectral-luminescence properties of 4,4′-di(2-oxazolyl)-stilbenes and 4,4′-di(2-oxazolyl)tolans

A new method is proposed for the synthesis of 4,4-di(2-oxazolyl)stilbenes and 4,4-di(2-oxazolyl) tolans by condensation of oxazolyl-substituted benzyl bromides or benzal dibromides under the influence of strong bases (KOH, potassium tertbutoxide) in dipolar aprotic solvents [dimethylformamide (DMF) and dimethyl sulfoxide (DMSO)]. The synthesized compounds luminesce intensely over the spectral range 386–492 nm.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 463–467, April, 1981.