Synthetic studies and characterization of some 1,3 diphenyl-2-propen-1-one"chalcones" having electron donating and electron withdrawing substituents

Abstract

Chalcones are members of a class of secondary metabolites called flavonoids. They can also be considered as open chain flavonoids in which two aromatic rings are joined by a three carbon unsaturated carbonyl system. They are widely distributed in plant kingdom. However these compounds can be synthesized in the laboratory using well established methods. In the present work Claisen-Schmidt condensation method was employed and as a result 40 compounds were synthesized which were classified under four series as mentioned below; A Series Chalcones: B-ring substituted Chalcones AI =1-Phenyl-3-( 4-methoxyphenyl)-2-propen-1-one A2 = 1-Phenyl-3-(3-methoxyphenyl)-2-propen-1-one A3 = 1-Pheny 1-3 -(2-methoxypheny 1)-2-propen-1-one A4 =1-Phenyl-3-(3 ,4-dimethoxyphenyl)-2-propen-1-one As = 1-Phenyl-3-(2-hydroxyphenyl)-2-propen-1-one A6 =1 -Phenyl-3-(3 -hydroxyphenyl)-2-propen-1-one A7 =1-Phenyl-3-( 4-hydroxyphenyl)-2-propen-1-one As = I-Phenyl-3-(2-chlorophenyl)-2-propen-1-one A9 =1-Phenyl-3-( 4-chlorophenyl)-2-propen-1-one AIO =lPphenyl-3-( 4-dimethylaminophenyl)-2-propen-1-one AII =1-Phenyl-3-( 4-diethylaminophenyl)-2-propen-1-one AI2 =1-Phenyl-3-(3-methylphenyl)-2-propen-1-one AI3 =1-Phenyl-3-( 4-methylphenyl)-2-propen-1-one AI4 =1-Phenyl-3-( 4-nitrophenyl)-2-propen-1-one B Series Chalcones: 2'-Methyl-B-ring substituted Chalcones BI= 1-(2' -Methylphenyl)-3-( 4-dimethylaminophenyl)-2-propen-1-one B2= 1-(2' -Methylphenyl)-3-( 4-dimethoxyphenyl)-2-propen-1-one B3= 1-(2' -Methylphenyl)-3-( 4-methoxyphenyl)-2-propen-1-one B4= 1-(2 ' -Methylphenyl)-3-( 4-methylphenyl)-2-propen-1-one C Series Chalcones: 2'-Hydroxy-B-ring substituted Chalcones CI= 1-(2' -Hydroxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one C2= 1-(2' -Hydroxyphenyl)-3-( 4-methoxyphenyl)-2-propen-1-one C3= 1-(2' -Hydroxyphenyl)-3-(3-methoxyphenyl)-2-propen-1-one C4= 1-(2 ' -Hydroxyphenyl)-3-phenyl-2-propen-1-one Cs= 1-(2' -Hydroxyphenyl)-3 -(2-chlorophenyl)-2-propen-l-one C6= 1-(2 ' -Hydroxyphenyl)-3-( 4-chlorophenyl)-2-propen- l -one C7= 1-(2' -Hydroxyphenyl)-3-( 4-fluorophenyl)-2-propen-l-one Cs= 1-(2 ' -Hydroxyphenyl)-3-( 4-methylphenyl)-2-propen-l-one C9= 1-(2' -Hydroxyphenyl)-3-(3- methylphenyl)-2-propen- l -one C 10= 1-(2' -Hydroxyphenyl)-3-( 4-dimethylaminophenyl)-2-propen-l -one C11= 1-(2 ' -Hydroxyphenyl)-3-(4-diethylaminophenyl)-2-propen-l-one C 12= 1-(2 ' -Hydroxyphenyl)-3-( 4-nitrophenyl)-2-propen-l -one D Series Chalcones: 5'-Chloro-2'-hydroxy-B-ring substituted Chalcones D1= 1-(5' -Chloro-2' -hydroxy phenyl)-3-phenyl-2-propen- l -one D2= 1-(5' -Chloro-2' -hydroxy phenyl)-3-(3-methoxylphenyl) -2-propen-l -one D3= 1-(5' -Chloro-2' -hydroxy phenyl)-3 -(4-methoxylphenyl)-2-propen- l -one D4= 1-(5' -Chloro-2' -hydroxy phenyl)-3-(3 ,4-dimethoxylphenyl)-2-propen- l -one Ds= 1-(5' -Chloro-2' -hydroxy phenyl)-3-( 4-chlorophenyl)-2-propen- l -one D6= 1-(5' -Chloro-2 ' -hydroxy phenyl)-3-(4-bromophenyl)-2-propen-l -one D7= 1-(5' -Chloro-2' -hydroxy phenyl)-3-( 4-fluorophenyl)-2-propen-l-one Ds= 1-(5' -Chloro-2' -hydroxy phenyl)-3-( 4-dimethylaminophenyl)-2-propen-l -one D9= 1-(5' -Chloro-2' -hydroxy phenyl)-3-( 4-methylphenyl)-2-propen- l -one DIO= 1-(5' -Chloro-2' -hydroxy phenyl)-3-(3-methylphenyl)-2-propen-l -one The physical data (%age Yield, m. p., Rr value, Solubility) were recorded and purity of each compound was checked by HPLC. Structures of these compounds were elucidated by spectroscopic tec1miques such as I.R, UV, IH NMR & ElMS.