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Chemical Research in Chinese Universities 2005年第3期21卷 274-279页

作者： XUJia-xi ZUOGang LIANGBo KeyLaboratoryofBioorganicChemistryandMolecularEngineeringofMinistryofEducation DepartmentofChemicalBiologyCollegeofChemistryandMolecularEngineeringPekingUniversity

Mass spectrometric behaviour of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide and 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide have been studied with the aid of mass-analyzed ion kinetic energy spectrometry and accurate mass measurements under electron impact ionization. The monooxide derivatives showed a tendency to eliminate an alkene or an oxygen atom. 1H-Azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide could also eliminate the thiophen-2-ylketene molecule via a reverse [2+2] cycloaddition. 2,3-Dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide could eliminate SO_2 or SO, respectively. The structure of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide was identified on the basis of its fragmentation. The identification was supported by the fragmentations of model compound, 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide.

关键词： 1H-Azeto[2,1-d]benzothiazepin-1-one 1,5-benzothiazepine Lactam Mass spectrometry

Synthesis and Crystal Structure of 2-p-Methyloxyphenyl- 3a-(2-phenyl-1,2,3-triazole-4-yl)-3,4-dihydro-1,2,4- oxa-diazolo[4,5-d][1,5] benzothiazepine

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Chinese Journal of Structural Chemistry 2007年第9期26卷 1061-1065页

作者：徐峰刘方明沈良刘罡杨春陈遒 College of Chemistry and Chemical Engineering Xinjiang University Department of Chemistry Hangzhou Teachers College 310036 China

The title compound2-p-methyloxyphenyl-3a-（2-phenyl-1,2,3-triazole-4-yl）-3,4- dihydro-1,2,4-oxa-diazolo[4,5-d][1,5] benzothiazepine （C31H25N5O2S, Mr = 531.63） has been synthesized and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1^- with a = 10.888（2）, b = 15.115（3）, c = 16.702（3）A, α = 99.90（3）, β = 95.21（3）, γ = 100.41（3）°, V = 2642.1（9） nm^3, Dc = 1.336 g/cm^3, Z = 4, F（000） = 1112, μ = 0.162 mm^-1 ,λ（MoKα） = 0.071073 nm, R = 0.0357 and wR = 0.1126 for 10620 observed reflections with I 〉 2σ（I）. X-ray analysis reveals that the molecular backbone consists of a tricyclic system with the central seven- membered ring in a twisted boat-like conformation.

关键词： 1,5-benzothiazepine 2-phenyl-1,2,3-triazole 1,2,4-oxadiazole crystal structure

Synthesis and Crystal Structure of an (N-Protected amino)-β-lactam Derivative of 1,5-benzothiazepine

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Chinese Journal of Structural Chemistry 2002年第2期21卷 133-135页

作者：张萍李旭张丽君李媛 Department of Chemistry Hebei Normal University Shijiazhuang 050016 China Department of Basic Course the Chinese Policimen Army College Langfang 102800 China

The title compound -(N-protected amino)--lactam (C36H33N2O5ClS), derivative of 1,5-benzothiazepine, was prepared by the reaction of 1,5-benzothiazepine 1 with (4R)- phenyloxazolidylacetyl chloride and characteized by X-ray diffraction analysis. The title compound crystallizes in orthorhombic system, space group P212121 with a=12.293(2), b=26.026(5), c=10.146(2)? V=3246.1?, Z=4, Dc=1.312g/cm3, Mr=641.15, F(000)=1344, μ= 0.228 mm1. The final R=0.0597 and wR=0.1165 for 3226 observed reflections with I ≥ 2?I). The crystal structure shows that the 4-phenyloxazolidyl and phenyl attached to C(8) and C(9) are in cis positions, and no trans product was discovered. So the cyclization to -lactam is stereospecific.

关键词： 1,5-benzothiazepine -lactam cycloaddition crystal structure

Synthesis and Steric Structure of 1, 5-benzothiazepine-Phenyl-β-Lactams

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Chinese Chemical Letters 1999年第1期10卷 23-26页

作者： Yuan LI Jian Dong SHI Yuan Jing ZHANG Sheng JIN Qi Yi XING(Department of Chemistry, Hebei Normal University. Shijiazhuang 050016 ShijiazhuangTeachers College 050041)(Beliing institute of Radiation Medicine, Beijing 100850)(Institute of Chemistry and Hebei Normal Univ Dept Chem Shijiazhuang 050016 Peoples R China Shijiazhuang Teachers Coll Shijiazhuang 050041 Peoples R China Beijing Inst Radiat Med Beijing 100850 Peoples R China Peking Univ Inst Chem & Mol Engn Beijing 100871 Peoples R China

1, 5-benzothiazepines 1 react with phenylacetyl chloride to give the title *** structures of these new compounds were confirmed by elemental analysis, ~1H NMR, ^(13)C NMRand MS spectroscopy, and their configuration (the mutual positions of the substituents relative to theβ-lactam ring) and conformation of the compounds were determined by X-ray crystal analysis.

关键词： 1,5-benzothiazepine β-lactam stereospecific reaction

The synthesis and biological evaluation of a series of novel 2-COOC_2H_5/COONa substituted 1,5-benzothiazepine derivatives as antimicrobial agents

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Chinese Chemical Letters 2009年第6期20卷 660-662页

作者： Ping Zhang Lan Zhi Wang Hui Shu Wu Jia Ming Lan Yuan Li Yong Xiang Wang The College of Chemistry & Material Science Hebei Normal University Shijiazhuang 050016 China Department of Pathogenic Biology Hebei Medical University Shijiazhuang 050017 China

A series of novel 1,5-benzothiazepine derivatives containing COOC2H5/COONa groups at the C（2）-position were synthesized and evaluated for their antifungal and antibacterial activities by both disc diffusion and minimal inhibition concentration （MIC） methods. Most of the compounds have been shown to have moderate to good antibacterial activity against S. aureus, S. epidermidis and excellent antifungal activity against C. albicans.

关键词： 1,5-benzothiazepine Antifungal Antibacterial activities

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

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One-pot synthesis of 2-aryl-3-acetyl-4-methyl-1,5-benzothiaz...

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

中国化学会·第十五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 are a kind of good physiological and pharmacological activities of heterocyclic *** classes of compounds have been known to show antiarrhythmic, antimicrobial, antioxidant, antiinflammatory, analgesics, antitumor, and anticonvulsant ***, many synthetic protocols have been developed to access diversied 1,5-benzothiazepines in past ***, a careful literature survey revealed that the majority of these protocols suffer from the drastic reaction conditions, low yields, cooccurrence of several side reactions, multistep reaction sequences, lengthy reaction *** scenario strongly suggests the development of a new methodology which meets the requirements of sustainable chemistry is still ***-pot synthesis method 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 of 2-aryl-3-acetyl-4-methyl-1,5-benzothiazepine was developed via domino reaction from aromatic aldehyde, acetylacetone and o-aminothiopheno as raw *** distinct advantages of our procedure are simple methodology, fast reaction rate, green reaction condition with good yields(80%-93%).The target compounds were determined by H NMR, C NMR, MS, IR and elemental *** synthetic route is shown in scheme1.

关键词： 1,5-benzothiazepine one-pot synthesis domino reaction

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

Further Investigation on the Rearrangement Mechanism of Reactions of 1,5-benzothiazepines with Ethoxycarbonylcarbene

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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Chemical Research in Chinese Universities 2006年第1期22卷 36-39页

作者： WU Chun-zan HUANG Jia-xing ZHANG Qi-han XU Jia-xi Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of Chemistry and Molecular Engineering Peking University Beijing 100871 P. R. China

The reactions of 2,3-dihydro-1,5-benzothiazepines with ethoxyearbonylcarbene undergo complex rearrangements to produce rlng-opening and ring contraction products. Previously it was presumed that the different products were formed via different mechanisms depending on the kind of substituents at the 2-position of 1,5-benzothiazepines. However, on the basis of the further detailed investigation, it was found that all 1,5-benzothiazepines can undergo the same rearrangement to yield both ring-opening and ring contraction products.

关键词： 1,5-benzothiazepine Ethoxycarbonylcarbene Rearrangement Ring-contraction Ring-opening