A Novel Synthesis of 2-Trichloromethylchromones and 7-Trichloromethylnorkhellin

Abstract

The reaction of 2-hydroxyacetophenones with trichloroacetyl chloride in the presence of pyridine at -30 °C followed by treatment of the reaction mixture with potassium tert-butylate affords 2-hydroxy-2-trichloromethylchroman-4-ones. Dehydration then provides the 2-trichloromethyl-chromones.

condensation - 2-hydroxyacetophenones - 2-hydroxy-2-trichloromethylchroman-4-ones - 2-trichloromethylchromones

References

1 Merchant JR. Bhat AR. Rege DV. Tetrahedron Lett.  1972,  2061 

2 Sosnovskikh VY. Ovsyannikov IS. Russ. J. Org. Chem.  1993,  29:  74 

3 Sosnovskikh VY. Mendeleev Commun.  1996,  189 

4 Sosnovskikh VY. Russ. Chem. Bull.  1998,  47:  354 

5 Sosnovskikh VY. Kutsenko VA . Ovsyannikov IS. Russ. Chem. Bull.  2000,  49:  478 

6 Meerwein H. Sönke H. Berichte  1931,  64:  2375 

7 Parham WE. Schweizer EE. J. Org. Chem.  1959,  24:  1733 

8 Moore RA. Levine R. J. Org. Chem.  1964,  29:  1883 

9 Sosnovskikh VY. Kutsenko VA. Mendeleev Commun.  1999, 206

10 Sosnovskikh VY. Kutsenko VA. Russ. Chem. Bull.  1999,  48:  2117 

11 Sosnovskikh VY. Mel’nikov MYu. Zh. Org. Khim.  1998,  34:  203 

12 Sosnovskikh VY. Kutsenko VA. Mendeleev Commun.  2000,  238 

13 Mashkovskii MD. In Lekarstvennye sredstva (Drugs)   Vol. 1:  Gamta; Vilnius: 1993.  p.396 

14 Kandil A. Galal EE. J. Drug Res.  1975,  7:  109 

15

Sosnovskikh, V. Ya.; Usachev, B. I.; Kodess, M. I. Izv. Akad. Nauk, Ser. Khim. 2002, in press.