Aqueous phase fly-ash catalyzed [4+2] Diels-Alder reaction of aryl enones and cyclopentadiene: Synthesis and insect antifeedant activities of aryl bicyclo [2.2.1] heptene-2-yl-methanones

Abstract

A series containing ten aryl 3-(substituted phenyl) bicyclo [2.2.1] heptene-2-yl-methanone derivatives including 3-(substituted phenyl) bicyclo [2.2.1]hepten-2-yl-(pyren-1-yl)-methanones have been synthesized by aqueous phase fly-ash catalyzed [4+2] Diels-Alder cyclo addition reaction of cyclopentadiene and aryl chalcones. The yields of the methanones are more than 60%. The synthesized methanones are characterized by their physical constants and spectral data. The insect antifeedant activities of synthesized methanones have been studied using Dethler's leaf-discs bioassay method.

Green approach using water mediated Diels-Alder reaction for the synthesis of some 2-(4-bromo-1-naphthyl)-3-(aryl) bicyclo[2.2.1]hept-5-ene methanones and evaluation of their antimicrobial and antioxidant activities

“…The synthesized ketones were characterized by their analytical data, physical constants (Table 1), and spectroscopic data, as follows. Based on earlier reports [1,3,4,9,[21][22][23][24][25] -1-yl)((1S,2S,3S,4R)-3-(3-bromophenyl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-chlorophenyl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-en-2-yl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-nitrophenyl) …”

“…The water mediated environmentally benign hetero Diels-Alder [4+2] cycloaddition reaction was 700 times faster than in nonaqueous phase [3]. Numerous catalysts were employed to perform this Diels-Alder reaction, such as specific and chiral Lewis acids [3,15], chiral bases [16], chiral amines [5,6], non-natural α-amino acids [17], bimodal catalysts [18], hydrogen bonding interactions [1], chiral silver phosphates [4], Ti(IV) compounds [19], alkaline salts [20], lithium perchlorate [10], pyridyl-modified RNA [11], fly-ash [21][22][23][24][25], carbocations [13], Cu(II) compounds [2], organo-tungstates with ionicliquids [26], ribozymes [27], low melting carbohydrates [28], and metal-free non-covalent compounds [29]. Fard et al have studied the solvent effect and performed DFT analysis of acid catalyzed Diels-Alder cycloaddition reaction of 2,5-dimethyl furan and maleic anhydride [30].…”