Open Access Open Access  Restricted Access Subscription Access

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

Viktoriia S. Moskvina, Sergii V. Shilin, Volodymir P. Khilya
Cover Image

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


Keywords


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

Full Text: PDF Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv