Chemistry of heteroanalogs of isoflavones

Condensation of cyanomethyl derivatives of benzimidazole and benzothiazole with resorcinol gave the corresponding 2,4-dihydroxy-α-hetarylacetophenones. The latter were converted to 3-hetarylchromones with methyl, trifluoromethyl, and ethoxycarbonyl groups in the 2 position or to chromones without substituents in this position.     

Chemistry of heteroanalogs of isoflavones

Pyrazole analogs of isoflavones were synthesized from substituted -(4-pyrazolyl)-2,4-dihydroxyacetophenones.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1108–1111, August, 1976.     

Chemistry of heteroanalogs of isoflavones

Condensation of 2-pyridylacetonitrile with polyphenols gave the corresponding -(2-pyridyl)-acetophenones, which were converted to the pyridine analogs of natural isoflavones and to 3-pyridylchromones with methyl, trifluoromethyl, and ethoxycarbonyl groups in the 2 position. The antimicrobial activity of 3-pyridylchromones and their reaction with alkylating and acylating agents and phosphorus pentasulfide were investigated.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1180–1185, September, 1977.     

Chemistry of heteroanalogs of isoflavones

It is shown that treatment of 3-hetarylchromones with alkalis and hydrazine hydrate leads to opening of the pyrone ring and subsequent conversion of the intermediate to -hetaryl-2-hydroxyacetophenones and 2-hydroxyphenylpyrazole derivatives.See [1] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1474–1476, November, 1976.     

Chemistry of heteroanalogs of isoflavones

3-Hetaryl-7-methoxychromones were obtained by reaction of -(5-ethoxycarbonyl-2-furyl)-, -(2-benzofuryl)-, and -(2-methoxy-carbonyl-5-benzofuryl)-2-hydroxy-4-methoxyacetophenones with methyl formate or ethyl orthoformate, and 3-hetaryl-4-hydroxy-7-methoxy-coumarins were obtained by reaction of the same compounds with diethyl carbonate. Methods for the synthesis of 3-hetaryl-7-hydroxy-chromones from -furyl- and -benzofuryl-substituted, 2,4-dihydroxyacetophenones were investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 174–179, February, 1975.     

Chemistry of heteroanalogs of isoflavones

Thiazole analogs of isomeric isoflavones were synthesized from -(2,4-dimethyl-5-thiazolyl)-2-hydroxyacetophenones, and their reaction with hydrazine hydrate and alkylating and acylating agents was studied. The reaction of thiazole derivatives of 7-hydroxychromone with hydrazine hydrate proceeds with opening of the pyrone ring and subsequent cyclization of the intermediate to o-hydroxyphenylpyrazole derivatives. The reaction of hydrazine hydrate with thiazole derivatives of 5-hydroxychromone, which proceeds with retention of the pyrone ring, leads to hydrazones. The structures of the new compounds were confirmed by the PMR spectra.See [1] for communication 6.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 25–28, January, 1979.     

Chemistry of the heteroanalogs of isoflavones

3-(1-Benzimidazolyl)chromones were obtained by the reaction of -(1-benzimidazolyl)-2,4-dihydroxy-5-ethylacetophenone with trifluoroacetic anhydride and acetic formic anhydride.For Communication 20, see [1].Taras Shevchenko National University. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1377–1379, October 1997.     

Chemistry of heteroanalogs of isoflavones 14. Isoxazole analogs of isoflavones

Isoxazole analogs of isoflavones have been synthesized by the cyclization of -(3-isoxazolyl)-2-hydroxyacetophenones. Their alkylation, acylation, and electrophilic substitution reactions, and reactions with binucleophiles have been studied. 3-(3-Isoxazolyl)-7-methoxychromones are rearranged selectively into 2-aminochromone derivatives by the action of hydroxylamine as a result of a double recyclization and are recyclized into pyrazole derivatives by hydrazine. Preparations with hypolipidemic, anabolic, hypoglycemic, and antiarrhythmic action are found among the derivatives of 3-(3-isoxazolyl)chromones.For Communication 13, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 29–39, January, 1993.     

Chemistry of heteroanalogs of isoflavones. 16. Benzthiazole analogs of isoflavones

The reaction of a-(2-benzthiazolyl)-2, 4-dihydroxy-5-alkylacetophenones with anhydrides and chlorides of carboxylic acids yielded 3-(2-benzthiazolyl)chromones with electron-acceptor and electron-donor substituents, as well as chromones unsubstituted in the 2 -position. Their acylation, alkylation, and aminoacylation reactions and their interaction with electrophilic and nucleophilic reagents were studied.Taras Shevchenko Kiev University, Kiev 252017. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 464–471, April, 1994. Original article submitted March 5, 1994.     

Chemistry of the heteroanalogs of isoflavones. 20. Benzimidazole analogs of isoflavones

3-(2-Benzimidazolyl)chromones with electron-donating and electron-withdrawing substituents and also chromones unsubstituted at position 2 were obtained by the reaction of alkyl--(2-benzimidazolyl)-2,4-dihydroxy-5-acetophenones with carboxylic acid anhydrides and chlorides. Reactions with cleavage and with retention of the pyrone ring were carried out.For Communication 19, see [1].Taras Shevchenko Kiev University, Kiev. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1237–1244, September, 1997.     

Chemistry of heteroanalogs of isoflavones 13. 1,3-Benzodioxan analogs of flavonoids

Some 1,3-benzodioxan analogs of chalcones and their epoxides have been obtained, and used to prepare pyrazolines and novel flavone and flavanone analogs of flavolignan (sylibin). The PMR spectra of novel compounds are shown and discussed, together with the results of preliminary biological tests.For Communication 12, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 879–887, July, 1992.     

Chemistry of heteroanalogs of isoflavones. 9. Reaction of thiazole analogs of isoflavones with nucleophilic and electrophilic reagents

Thiazole analogs of isoflavones and their 4-thioxo derivatives undergo recyclization to pyrazole derivatives and isomeric isoxazoles under the influence of hydrazine, methylhydrazine, phenylhydrazine, and hydroxylamine. A new group enters the 8 position or two groups simultaneously enter the 6 and 8 positions of the chromone ring in electrophilic substitution reactions. Data from the PMR spectra and on the biological activity are presented and discussed.See [1] for Communication 8.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 321–327, March, 1982.     

Chemistry of heteroanalogs of isoflavones. 23. Synthesis of aminoacyl derivatives of 3-phenoxychromone

Reaction of Boc-protected amino acids with 3-phenoxy-2-trifluoromethylchromones gave new, previously unknown aminoacyl derivatives.T. G. Shevchenko Kiev University, Kiev 252033, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 744–748, June, 1999.     

Chemistry of isoflavone heteroanalogs.

Benzodioxane analogs of chalcones were isomerized to the corresponding flavanones and isoflavones. The PMR and IR spectra of these compounds were discussed.For Communication 11, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 319–323, March, 1989.     

Chemistry of heteroanalogs of isoflavones. 8. Reaction of benzofuran analogs of isoflavones and their 4-thioxo derivatives with hydroxylamine and hydrazine

A number of 3-(2-benzofuryl)-6-ethylchromones and their 4-thioxo derivatives were synthesized, and the action of hydroxylamine and hydrazine on them was investigated. Isomeric 3 (5)-(o-hydroxyphenyl) isoxazoles were obtained in the reaction with hydroxylamine. The predominant formation of one or the other isomer depends on the character of the substituents in the 2 and 4 positions of the chromone. The reaction of chromones with hydrazine leads to o-hydroxyphenylpyrazoles. The compounds obtained were characterized by their IR, UV, and PME spectra.See [ 1] for Communication 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 892–897, July, 1981.     

Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone,flavone, and isoflavone

Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan — silibin — have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed.For article 10, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–198, February, 1986.     

Chemistry of the hetero analogs of isoflavones. 22. Mannich reaction in the benzimidazole and benzothiazole analogs of isoflavones

New 3-(2-benzothiazolyl)chromones were obtained by the reaction of 2-(2,4-dihydroxy-5-ethylphenacyl)-benzothiazole with triethyl orthoformate or carboxylic acid anhydrides. Aminomethylation of the chromones and also of familiar 3-(2-benzimidazolyl)chromones by substituted 1,1-diaminomethanes gave Mannich bases.For Communication 21, see [1].Taras Shevchenko Kiev University, Kiev, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1072–1078, August, 1998.     

Aziridinyl ketones and their heteroanalogs

5-Aryl-7-(4-nitrophenyl)-1,4-diazabicyclo[4.1.0]hepta-4-enes (I), which have photochromic properties, were synthesized. The structures of the compounds were confirmed by data from the IR, PMR, and mass spectra. The acidolysis of I was investigated, and it was assumed that the mechanism of the reaction includes diprotonation of the bases, while the primary process is the formation of immonium salts. The structures of the photocolored forms of the salts and bases are discussed.See [1] for communication 1.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 536–540, April, 1979.     

Electronic absorption spectra of styrene heteroanalogs

Conclusions The UV bands for styrene heteroanalogs, as in the case of butadiene heteroanalogs, are shifted toward longer wavelengths upon the introduction of several heteroatoms into one fragment and toward shorter wavelengths upon the introduction of the heteroatoms into different fragments.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2585–2586, November, 1987.     

Analysis of electronic spectra of butadiene heteroanalogs

Conclusions The effect of replacing the carbon atoms by heteroatoms on the electronic spectrum of butadiene and its heteroanalogs was discussed, and a rule was proposed that permits predicting the behavior of the -^* bands of these compounds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 450–454, February, 1984.