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An efficient one-pot synthesis of 2-carboxyl-3-ester-1,5-benzodiazepines catalyzed by γ-Fe2O3@SiO2-CeCl3 as an recyclable catalyst

Bei Yue-ming  Liu Qian-nan  Wang Lan-zhi  
【摘要】:1,5-Benzodiazepines have been an important pharmacophore in the pharmaceutical industry.These compounds are widely used as antianxiety,anticonvulsant and antibacterial agents[1].Due to their wide range of pharmacological activities especially its antimicrobial activity,the development of practical and green protocols continues to be a challenging endeavour in synthetic chemistry.Previous studies on 1,5-benzodiazepines have indicated that the free ester group present at different positions in the nuclei of the molecules could enhance the pharmacological properties of the compounds,and this effect is attributed to their high hydrophobicity[2].Moreover,carboxyl group is also known to be an important scaffold in many potent biologically active molecules.So we wished to examine the possibility of synthesis of 1,5-benzodiazepines incorporating free carboxyl and ester moiety on the seven-membered ring structure.Herein,we report an efficient one-pot synthesis of a novel series of 2-carboxyl-3-ester-1,5-benzodiazepines under mild condition(Et OH as solvent).The target compounds were obtained via the condensation reaction of β-ketonic ester(2 a-2 c) with substituted o-phenylenediamine(1 a-1 b) and glyoxylic acid(4) in the presence of γ-F_e2O_3@SiO_2-CeCl_3(Scheme 1).The structures of the synthesized compounds were characterized by ~1H NMR,~(13)C NMR,MS,IR and elemental analysis.The distinct advantages of our procedure are simple methodology,fast reaction rate,green reaction condition with good yields(80%-85%) and the γ-Fe_2O_3@SiO_2-CeCl_3 catalyst was used directly four times without a considerable loss of its catalytic activity.

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