SYNTHESIS AND CHARACTERIZATION ARYLIDENE-4-ARYL- BUT-3-EN-4-0LIDES

Abstract

Butenolides and their derivatives are known to possess a wide range of biological activities. In the present work two series of butenolides were synthesized pertaining to 26 compounds in total. These consist of seventeen compounds of A-series ie 2- arylidene-4-( 4-ethoxy phenyl)but-3-en-4-olides and nine compounds of B-series ie 2- arylidene-4-( 4-bromo phenyl)but-3-en-4-olides. These compounds were synthesized by condensing 3-( 4-substituted benzoyl)propionic acid with appropriate aromatic aldehydes in the presence of triethyl amine in acetic anhydride. These compounds were purified by using recrystallization and were characterized completely on the basis of their physical and spectral data (IR, lB, l 3C NMR, Mass) as well as elemental analysis results. The general structure of the synthesized compounds and their names are as follows: R o A-Series 2-Arylidene-4-( 4-ethoxy phenyl)but-3-en-4-olides B-Series 2-Arylidene-4-( 4-bromo phenyl)but-3-en-4-olides A-Series: B02C B04C B03B B04B B02F B03F B04F 2-(2-Chlorobenzylidene )-4-( 4-ethoxy phenyl)but-3-en-4-olide 2-( 4-Chlorobenzylidene )-4-( 4-ethoxy phenyl)but-3-en-4-olide 2-(3 -Bromo benzylidene )-4-( 4-ethoxy phenyl)but -3-en-4-0Iide 2-( 4-Bromobenzylidene )-4-( 4-ethoxy phenyl)but-3-en-4-0Iide 2-(2-Florobenzylidene )-4-( 4-ethoxy phenyl)but-3-en-4-0Iide 2-(3 -Florobenzylidene)-4-(4-ethoxy phenyl)but-3-en-4-0Iide 2-(4-Florobenzylidene )-4-( 4-ethoxy phenyl) but -3 -en-4-0Iide VI B02M B03M B04E B02H B03H B04H B02N B03N B04N B04T B-Series: BB02C BB04C BB03B BB04F BB03M BB02H BB03N BB04N BB04T 2-(2-Methoxybenzylidene )-4-( 4-ethoxy phenyl) but -3-en-4-olide 2-(3 -Methoxybenzy1idene )-4-( 4-ethoxy phenyl )but-3 -en-4-olide 2-( 4-Ethoxybenzy1idene )-4-( 4-ethoxy phenyl)but-3-en-4-olide 2-(2-Hydroxybenzy lidene )-4-( 4-ethoxy phenyl) but-3-en-4-olide 2-(3 -Hydroxybenzylidene )-4-( 4-ethoxy phenyl) but-3 -en-4-olide 2-( 4-Hydroxybenzylidene )-4-( 4-ethoxy phenyl)but-3 -en-4-o1ide 2-(2-Nitrobenzylidene)-4-(4-ethoxy phenyl)but-3-en-4-olide 2-(3-Nitrobenzylidene)-4-(4-ethoxy phenyl)but-3-en-4-o1ide 2-(4-Nitrobenzylidene)-4-(4-ethoxy phenyl)but-3-en-4-olide 2-(4-Methy1benzylidene)-4-(4-ethoxy phenyl)but-3-en-4-olide 2-(2-Ch1oro benzylidene )-4-( 4-bromo phenyl) but-3 -en-4-olide 2-( 4-Ch1oro benzylidene )-4-( 4-bromo phenyl) but -3-en-4-olide 2-(3-Bromobenzylidene )-4-( 4-bromo phenyl)but-3-en-4-o1ide 2-(4-Florobenzylidene )-4-( 4-bromo phenyl)but-3-en-4-olide 2-(3 -Methoxybenzylidene )-4-( 4-bromo phenyl) but-3 -en-4-olide 2-(2-Hydroxybenzy1idene )-4-( 4-bromo phenyl)but-3 -en-4-o1ide 2-(3-Nitrobenzylidene )-4-( 4-bromo phenyl)but-3-en-4-olide 2-( 4-Nitrobenzylidene )-4-( 4-bromo phenyl)but-3-en-4-o1ide 2-(4-Methy1benzylidene)-4-(4-bromo phenyl)but-3-en-4-o1ide