Synthesis, characterization and antimicrobial activities of some fluorine containing 2-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)-3-chloro­chromones, 2-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)chromones and 5-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)-3-(2-hydroxyphenyl)-4,5-dihydropyrazolines

Abstract

Base catalyzed condensation of <b style="">1</b> with <b style="">2</b>gives compound <b style="">3 </b>[1-(5-fluoro-2-hydroxyphenyl)-3-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)-2-propen-1-one]. On oxidative cyclization with DMSO-CuCl₂ <b style="">3 </b>gives 2-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)-3-chloro-6-fluoro­chro­­m­­ones <b style="">4</b>.<b style=""> </b>On cyclization with DMSO-I₂, <b style="">3</b> gives 2-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)- 6-fluorochromones <b style="">5</b>.<b style=""> </b>When <b style="">3 </b>is heated with hydrazine in dioxane gives <b style="">6 </b>[5-(1-phenyl-3-aryl-1<i>H</i>-pyrazol-4-yl)-3-(5-fluoro-2-hydroxyphenyl)-4,5-dihydropyra­zo­lines.<b style=""> </b>The pro­­ducts <b style="">3</b>, <b style="">4, 5 </b>and <b style="">6 </b>are characterized by spectral and elemental analysis. Compounds <b style="">3</b>,<b style=""> 4</b> and <b style="">6</b> are tested for their antimicrobial activities.