CONDENSATION OF 2-(4-CHLOROPHENYL)-1-(2,4-DIHYDROXYPHENYL)ETHANONE WITH <i>N</i>,<i>N</i>-DIMETHYLFORMAMIDE DIMETHYL ACETAL: AN EFFECTIVE APPROACH TO 3-(4-CHLOROPHENYL)-7-METHOXY-4<i>H</i>-CHROMEN-4-ONE, N,O- AND N,N-HETEROCYCLES

Authors

  • Viktoriia S. Moskvina Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033
  • Sergii V. Shilin Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033
  • Volodymir P. Khilya Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033

DOI:

https://doi.org/10.1007/2617

Keywords:

deoxybenzoin, N, N-dimethylformamide dimethyl acetal, enamino ketone, 2-hydroxydeoxybenzoin, isoflavone, heterocyclization

Abstract

A convenient sequence for the preparation of 2-(4-chlorophenyl)-1-(2,4-dimetoxyphenyl)- 3-(dimethylamino)prop-2-en-1-one has been developed. It  has been demonstrated that the use of 1-(2,4- dihydroxyphenyl)ethanone or 1-(2-hydroxy-4-methoxyphenyl)ethanone in a condensation reaction with N,N-dimethylformamide dimethyl acetal leads to their heterocyclization to give an isoflavone. Reactions of the enamino ketone with N,O- and N,N-binucleophiles have been studied; as the result, 4,5-diarylisoxazole, 4,5-diarylpyrazoles, and 4,5-diaryl-substituted 2-aminopyrimidine have been obtained in good yields.

How to Cite
Moskvina, V. S.; Shilin, S. V.; Khilya, V. P. Chem. Heterocycl. Compd. 2015, 51, 799. [Khim. Geterotsikl. Soedin. 2015, 51, 799.]

For this article in the English edition see DOI 10.1007/s10593-015-1777-3

Author Biographies

Viktoriia S. Moskvina, Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033

Viktoriia Sergiivna Moskvina

Sergii V. Shilin, Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033

Sergii Volodymirovych Shilin

Volodymir P. Khilya, Kyiv National Taras Shevchenko University, 60 Volodymyrska St., Kyiv 01033

Volodymir Petrovych Khilya

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Published

2015-10-13

Issue

Vol. 51 No. 9 (2015)

Section

Original Papers