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. 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

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.