Synthesis of benzofuran containing ketones and their derivatives from the reaction of chloromethylketones with 2-hydroxybenzaldehydes

In this study, mesitylene and benzofuran rings containing new ketones were synthesized from thereaction of 1-chloro-3-mesitylacetone with salicylaldehyde, 5-bromo salicylaldehyde, 3-methoxysalicylaldehyde and 2-hydroxy benzonitrile in different appropriate solvents. In these reactions, severalbases, such as NaOH, K2CO3, and NaH were used as neutralizing agents.1-(3-Aminobenzofuran-2-yl)-2-mesitylethanone which was synthesized from 2-hydroxy-benzonitrile and 1-chloro-3-mesitylacetone, was converted its novel amides by using with different acylhalogens. These acyl halogenes are mainly acetyl chloride, propanoyl chloride, benzoyl chloride andphenylacetyl chloride.Bisbenzofuran-2-yl-ketone was synthesized with two different methods. In the first method, 2-acetylbenzofuran which was synthesized from salicyl aldehyde and 1-chloroacetone, brominated on themethyl group of compound so as to obtain 2-(bromoacetyl)benzofuran. This new haloketone was convertedinto bis(benzofuran-2-yl)methanone with salicyl aldehyde in the presence of NaH. In the second method;bis(benzofuran-2-yl)methanone was directly synthesized from the reaction of 1,3-dichloroacetone andsalicyl aldehyde in the presence of K2CO3 . Yields of the two method are more or mately less same andsatisfactory.Obtained benzofuran ketones were converted into their semicarbazone, alcohol and oximederivatives. Ketoksimes were used in the synthesis of new oxime ethers and esters with appropriate alkyland acyl halogens in absolute acetone solvent in the presence of K2CO3 as neutralizing agent.The structure of the compounds have been characterized by mainly FT-IR, 1H-13C-NMRspectroscopy techniques. X-ray diffraction pattern of some selected compounds were obtained and given inthe thesis. Melting points were obtained by using DSC technique. Elemental analyses results were alsofound to be in good agreement with the determined structures.Keywords: Mesitylene, benzofurans, semicarbazones. oximethers, oximesters.