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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

An efficient one-pot synthesis of 2-carboxyl-3-ester-1,5-ben...

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Bei Yue-ming Liu Qian-nan Wang Lan-zhi The College of Chemistry and Material Science Hebei Normal University

1,5-Benzodiazepines have been an important pharmacophore in the pharmaceutical *** 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 *** 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 *** we wished to examine the possibility of synthesis of 1,5-benzodiazepines incorporating free carboxyl and ester moiety on the seven-membered ring ***,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-F2o@sio-cecl(Scheme 1).The structures of the synthesized compounds were characterized by H NMR,C NMR,MS,IR and elemental *** distinct advantages of our procedure are simple methodology,fast reaction rate,green reaction condition with good yields(80%-85%) and the γ-feo@sio-cecl catalyst was used directly four times without a considerable loss of its catalytic activity.

关键词： γ-fe2o3@sio2-cecl3 one-pot 1,5-benzodiazepine

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one-pot synthesis of 2-aryl-3-benzoyl-4-methyl-1,5-benzothiazepine compounds via domino reaction

One-pot synthesis of 2-aryl-3-benzoyl-4-methyl-1,5-benzothia...

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中国化学会·第十六届全国有机合成化学学术研讨会

作者： Haitao Wu 王兰芝 The College of Chemistry and Material Science Hebei Normal University 河北师范大学

1,5-benzothiazepines is an important class of heterocyclic compounds with good physiological and pharmacological *** compounds have been known to show anti arrhythmic,antimicrobial,antioxidant,antiinflammatory,analgesics,antitumor,and anticonvulsant ***,many synthetic protocols have been developed to access diverse 1,5-benzothiazepines in past ***,a careful literature survey revealed that the majority of these protocols suffer from the drastic reaction conditions,low yields and occurrence of several side reactions,multistep reaction sequences and lengthy reaction *** scenario strongly suggests the development of a new methodology which meets the requirements of sustainable chemistry is still ***-pot synthesis method via domino reaction can realize multiple reaction processes or multiple operations in the same reactor to obtain highly selective target compounds,avoiding tedious separation and purification,which is a simple operation,environment friendly,and high atomic economy synthesis ***,a new approach for the one-pot synthesis of2-aryl-3-benzoy 1-4-methyl-1,5-benzotbiazepine was developed via domino *** target compounds with enamine stucture(5 aa-5 bc) and imine stucture(5 bd-5 be) were obtained via a series of domino reaction of aromatic aldehyde(1 a-e) with benzoylacetone(2) and substituted o-aminothiophenol(4 a-b) in the presence ofγ-fe o@*** distinct advantages of our procedure are simple methodology,fast reaction rate,green reaction condition with good yields(82%-90%).In addition,the y-fe o@sio-cecl catalyst was used directly five times without a considerable loss of its catalytic *** target compounds were determined by H NMR,C NMR,MS,IR and elemental *** synthetic route is shown in scheme 1.

关键词： 1,5-benzothiazepine γ-fe2o3@sio2-cecl3 one-pot synthesis

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