Synthesis and insect antifeedant activities of some substituted styryl 3,4-dichlorophenyl ketones

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Abstract

Sixteen substituted styryl 3,4-dichlorophenyl ketones [(2E)-1-(3,4-dichlorophenyl)-3-phenyl-2-propen-1-ones] were synthesized using eco-friendly benign stereoselective crossed-aldol reaction. They are characterized by their analytical, infrared, NMR and mass spectral data. The insect antifeedant activities of these chalcones were evaluated using Caster semilooper and Achoea janata L.

Introduction

Green chemistry provides good eco-friendly methods for synthesis of organic compounds without solvent. Among these methods the aqueous phase reaction is very interesting due to operative simplicity, easy work up, good yield, non-hazardous conditions and being safer for the environment. Chemists and environmental scientists have reported various solvent methods for organic synthesis. The use of bases for synthesis of chalcones with or without solvent is important [1]. A literature survey reveals that there are few papers reporting synthesis of chalcones using bases in aqueous phase aldol condensation reaction between ketones and aldehydes. Various reagents are used for solvent free synthesis like, metals and metal chelates [2], carbonates [3], chiral boronate ester [4], phosphate [5], organolithium [6], sodium hydroxide [7], silica-sulphuric acid [8], alumina [9], organic ionic liquids [10], metal-nanoparticles [11] and potassium hydroxide-ethanol [12]. Kalluriya and Ray [13] synthesized sydenone chalcones with more than 60% yield using grinding of aqueous sodium hydroxide-heterogeneous reaction medium with aldehydes. Hassen and co-workers [14] reported more than 60% yield of some heteroaryl chalcones obtained by the solvent free reaction with aldehydes in 20 °C cooling condition in presence of surfactants. Venkat Reddy et al. [15] reported more than 70% yield of chalcones synthesized using zinc chloride and microwave techniques. Thirunarayanan [16] reported aqueous potassium hydroxide used as a reagent for synthesis of some aryl chalcones by grinding aryl aldehydes and ketones. The authors wish to report an efficient and selective method for condensation of 3,4-dichlorophenyl methyl ketones with various m- and p-substituted benzaldehydes under solvent free conditions by stirring the reactants with sodium hydroxide at room temperature to yield the respective E-2-propen-1-ones. Studies of quantitative structure property relationship and insect antifeedant activities are likewise reported. In this method during stirring of 3,4-dichloro acetophenone and aldehydes, they decomposed slowly forming the products in good yield and the reaction time is lower than in the solution phase thermal method. The methylene units of chalcones derived from cyclic or acyclic ketones are found in many naturally occurring compounds and they are useful for the synthesis of pyrimidine derivatives [17]. The basic skeleton of chalcones is widely represented in natural products and are known to have multipronged activity [18]. Many of the chalcones are used as agrochemicals and drugs [19].

Section snippets

Experimental

All chemicals used were purchased from Sigma–Aldrich and E-Merck chemical company. Melting points of all chalcones were determined in open glass capillaries on Mettler FP51 melting point apparatus and are uncorrected. Infrared spectra (KBr, 4000–400 cm−1) were recorded on AVATAR-300 Fourier transform spectrophotometer. INSTRUM AV300 operating at 500 MHz for 1H spectra and 125.46 MHz for 13C spectra in CDCl3 solvent using TMS as internal standard. Electron impact (EI) (70 eV) and chemical ionization

Results and discussion

Our previous investigations [20], [21], [22], [23], [24], [25] deal with to carbon–carbon bond formation and we studied in this article the crossed-aldol condensation of 3,4-dichloroacetophenone and a variety of different substituted aryl aldehydes. This occurs in water at room temperature and in the presence of cetyltrimethylammonium bromide (CTABr) as the proper cationic surfactant for the synthesis of (2E)-1-(3,4-dichlorophenyl)-3-phenyl-2-propen-1-ones in an excellent yield with high

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