期刊信息

  • 刊名： 河北师范大学学报（自然科学版）Journal of Hebei Normal University (Natural Science)
  • 主办： 河北师范大学
  • ISSN： 1000-5854
  • CN： 13-1061/N
  • 中国科技核心期刊
  • 中国期刊方阵入选期刊
  • 中国高校优秀科技期刊
  • 华北优秀期刊
  • 河北省优秀科技期刊

协同采编系统

友情链接

1,5-苯并硫氮䓬杂类化合物合成研究的新进展

  • 河北师范大学 化学与材料科学学院,河北省有机功能分子重点实验室,河北 石家庄 050024
  • DOI： 10.13763/j.cnki.jhebnu.nse.202103016

Research Progress of Synthesis of 1, 5-benzothiazepines

摘要/Abstract

摘要：

1,5-苯并硫氮杂䓬类化合物是一类具有多种生理活性的七元杂环化合物,是医药、化工产品以及功能化材料的关键中间体，因此其合成方法的研究一直是有机化学及药物化学的热点之一. 归纳了近年来1,5-苯并硫氮䓬杂类化合物的合成方法及各类合成反应的特点，并对其合成及应用前景进行展望.

Abstract：

1, 5-benzothiazepine compounds are a class of seven-membered heterocyclic compounds with various physiological activities, which are key intermediates for pharmaceuticals, chemicals and functional materials. Consequently, the study on their synthesis methods has been one of the hot spots in organic and pharmaceutical chemistry. In this paper, the research progress on synthesis methods of 1, 5-benzothiadiazepine compounds in recent years is reviewed. The characteristics of various synthesis reactions are analyzed, and the development trend of 1, 5-benzothiadiazepine compounds in the future is also discussed.

关键词

关键词： 1,5-苯并硫氮杂䓬类化合物 ; 合成 ; 研究进展
Key words： 1,5-benzothiazepine compounds ; synthesis ; progress

参考文献 31

  • [1] WANG Y, KONG L, WANG R, et al. Synthesis and Antimicrobial Activity of C(3)-1, 2, 4-triazolyl-1, 5-benzothiazepines [J] . Org Lett，2019, 39(9):2663-2670. doi:10. 6023/cjoc201901041
  • [2] CORTI V, GONZALEZ P C, FEBVAY J, et al. Organocatalytic Asymmetric Sulfa-michael Addition of 2-amin-othiophenols to Chalcones:First Enantioselective Access to 2, 3, 4, 5-tetrahydro-1, 5-benzothiazepines [J] . Eur J Org Chem，2017(1):49-52. doi:10. 1002/ejoc. 201601364
  • [3] RAHMAN M, ROY A, MAJEE A, et al. Synthesis of 1, 5-benzothiazepines with Microwave Irradiation Under Solvent and Catalyst:Free Conditions [J] . J Chem Res，2009(3):178-179. doi:10. 3184/030823409x416965
  • [4] BERESTOVITSKAYA V M, BAICHURIN R I, ABOSKALOVA I, et al. New Approaches to the Synthesis of 2, 5-dihydro-1, 5-benzothiazepines Containing Nitro Groups [J] . Mendeleev Commun ，2014, 24(6):380-382. doi:10. 1016/j. mencom. 2014. 11. 025
  • [5] CHATE A V, JOSHI R S, BADADHE P V, et al. Efficient Ultrasound Enhance Novel Series of 2-((E)-2, 3-dihydro-2-(4-(phenylthio)phenyl)benzo [b] [1, 4] thiazepin-4-yl)phenol as an Antimicrobial Agent [J] . Bull Korean Chem Soc， 2011, 32 (11):3887-3892. doi:10. 5012/bkcs. 2011. 32. 11. 3887
  • [6] ALBANESE D C M, GAGGERO N, FEI M. A Practical Synthesis of 2, 3-dihydro-1, 5-benzothiazepines [J] . Green Che， 2017, 19(23):5703-5707. doi:10. 1039/c7gc02097j
  • [7] KUMAR M, SHARMA K, FOGLA A K, et al. Synthesis and Antimicrobial Activity of 2, 4-diaryl-2, 3-dihydrobenzo [b] [1, 4] thiazepines [J] . Res Chem Intermed，2013, 39(6):2555-2564. doi:10. 1007/s11164-012-0782-8
  • [8] ACHARYA A P, KAMBLE R D, PATIL S D, et al. "Green Synthesis"of Benzothiazepine Library of Indeno Analogues and Their in Vitro Antimicrobial Activity [J] . Chem Pap，2014, 68(5):719- 724. doi:10. 2478/s11696-013-0496-4
  • [9] CHEN S Q, DING F, LIU F M. Investigation on the Ring-opening Reactions of 3-(1H-1, 2, 4-triazol-1-YL)1, 5-benzothiazepines with Arylonitrile Oxides [J] . Phosphorus Sulfur Silicon Relat Elem，2011, 186(3):574-581. doi:10. 1080/10426507. 2010. 509290
  • [10] MOR S, PAHAL P, NARASIMHAN B. Synthesis, Characterization, Biological Evaluation and QSAR Studies of 11-p-substitutedPhenyl-12-phenyl-11a, 12-dihydro-11H-indeno [2, 1-c] [1, 5] benzothiazepines as Potential Antimicrobial Agents [J] . Eur J Med Chem，2012, 57:196-210. doi:10. 1016/j. ejmech. 2012. 09. 003
  • [11] GHANDI M, MOMENI T, NAZERI M T, et al. A One-pot Three-component Reaction Providing Tricyclic 1, 4-benzoxazepine Derivatives [J] . Tetrahedron Lett，2013, 54(23):2983-2985. doi:10. 1016/j. tetlet. 2013. 03. 131
  • [12] XU T, WANG R, ZHANG P. Synthesis of Ethyl 2-substituted Phenyl-4-phenyl-1, 5-benzothiazepine-3-formate [J] . Chem Reagents，2018, 40(9):888-892. doi:10. 13822/j. cnki. hxsj. 2018. 09. 016
  • [13] MENINNO S, VOLPE C, LATTANZI A. Catalytic Enantioselective Synthesis of Protecting-group-free 1, 5-benzothiazepines [J] . Chem-Eur J，2017, 23(19):4547-4550. doi:10. 1002/chem. 201700837
  • [14] SUN P, FANG L, WU L. An Efficient Synthesis of 1, 5-benzothiazepines in the Presence of Sub-stoichiometric Amount of Cyanuric Chloride [J] . J Sulfur Chem，2011, 32(3):257-261. doi:10. 1080/17415993. 2011. 572971
  • [15] HMUILOVICH K S, ORLOVA N A, BEREGOVAYA I V, et al. Reactions of Polyfluorinated Chalcones with o-aminobenzenethiol and Its Zinc Salt [J] . Russ Chem Bul, 2011, 60(2):361-367. doi:10. 1007/s11172-011-0058-2
  • [16] KIDWAI M, PODDAR R, JAIN A, et al. Synthesis and SARs of Coumarin Fused 1, 5-benzothiazepines as Novel Anticancer and Antioxidant Agents [J] . Mini-Rev Org Chem，2015, 12(1):24 -33. doi:10. 2174/1570193x11666141029004602
  • [17] PAN X Q, ZOU J P, HUANG Z H, et al. Ga(OTf)3-promoted Condensation Reactions for 1, 5-benzodiazepines and 1, 5-benzothiazepines [J] . Tetrahedron Lett，2008, 49(36):5302-5308. doi:10. 1016/j. tetlet. 2008. 06. 082
  • [18] KAISHAP P P, SHEKARRAO K, SAIKIA P, et al. A Facile Synthesis of Benzo [b] 1, 4-thiazepine Derivatives by Palladium Acetate Catalyzed Reaction [J] . Tetrahedron Lett，2014, 55 (11):1927-1930. doi:10. 1016/j. tetlet. 2014. 01. 153
  • [19] YADAV T, KUMAR M, JAIN R, et al. A Novel Ionic Liquid Mediated Synthesis of 2, 3-dihydro-1, 5-benzothiazepines Using Recycleable Catalyst Amberlyst-15 (R) [J] . Indian J Chem Sect B ：Org Chem Incl Med Chem，2012, 51(10):1447-1451. doi:10. 1002/chin. 201307168
  • [20] FARGHALY T A, HASSANEEN H M E. H-ferrierite Zeolite:As an Effective and Reusable Heterogeneous Catalyst for Synthesis of 1, 5-benzothiazepine Under Solvent Free Condition and 1, 3-dipolar Cycloaddition in Water [J] . Arab J Chem， 2017, 10:S3255-S3262. doi:10. 1016/j. arabjc. 2013. 12. 024
  • [21] SHARIFI A, HOSSEINI F, GHONOUEI N, et al. Reactions of 2-aminothiphenols with Chalcones in an Ionic Liquid Medium:A Chemoselective Catalyst-free Synthesis of 1, 5- benzothiazepines [J] . J Sulfur Chem，2015, 36(3):257-269. doi:10. 1080/17415993. 2015. 1014483
  • [22] FUKATA Y, YAO K, MIYAJI R, et al. Asymmetric Net Cycloaddition for Access to Diverse Substituted 1, 5-benzothiazepines [J] . J Org Chem，2017, 82(23):12655-12668. doi:10. 1021/acs. joc. 7b02451
  • [23] MOHAMED M A A. Utility of Alpha-oxoketene and Alpha-cyanoketene Thioacetals in Heterocyclic Syntheses:Synthesis of Some New Benzothiazepine Erivatives [J] . Synth Commun， 2011, 41(3):331-340. doi:10. 1080/00397910903538644
  • [24] YAN Y, YANG X, WU L. Facile Synthesis of 1, 5-benzothiazepines in Water Using Tetrabutylammonium Tribromide [J] . Phosphorus Sulfur Silicon Relat Elem，2012, 187(5):573-579. doi:10. 1080/10426507. 2011. 627900
  • [25] WU X L, LIU F M, ZHOU Y L. Synthesis and Structure Characterization of New 1, 2, 4-triazolo [5, 4-d] [1, 5] benzothiazepine Derivatives Through 1, 3-dipolar Cycloaddition Reaction [J] . J Heterocycl Chem，2011, 48(2):368-372. doi:10. 1002/jhet. 587
  • [26] KLIMOVA E I, GALLARDO V M A, SANCHEZ G J J, et al. 4-aryl-2-ferrocenyl- and 2-aryl-4-ferrocenyl-2, 3-dihydro-1, 5-benzothiazepines with Potentially Biological Activities:Synthesis, Characterization, X-ray Diffraction Studies [J] . J Heterocycl Chem，2016, 53(6):1990-1998. doi:10. 1002/jhet. 2519
  • [27] CHATE A V, JOSHI R S, MANDHANE P G, et al. An Improved Procedure for the Synthesis of 1, 5-benzothiazepines Using Ceric Ammonium Nitrate(CAN) [J] . J Heterocycl Chem，2011, 55 (5):776-780. doi:10. 5012/jkcs. 2011. 55. 5. 776
  • [28] DANDIA A, SINGH R, SINGH D, et al. Regioselective Synthesis of Diltiazem Analogue Pyrazolo 4, 3-c 1, 5-benzothiazepines and Antifungal Activity [J] . Phosphorus Sulfur Silicon Relat Elem，2010, 185(12):2472-2479. doi:10. 1080/10426501003713064
  • [29] LOGHMANI-KHOUZANI H, TAMJIDI P, MOHAMMADPOOR-BALTORK I, et al. Efficient and Eco-friendly Syntheses of 1, 5-benzothiazepines and 1, 5-benzodiazepines Catalyzed by [Hmim] NO3 Under Mild Conditions [J] . J Heterocycl Chem，2014, 51(1):138-150. doi:10. 1002/jhet. 1827
  • [30] LIU Q, LI W, QIU Z, et al. Michael Addition of Aminothiophenols to Alpha, Beta-unsaturated Ketones with High Steric Hindrance Catalyzed by CeCl3 Center Dot 7H2O-NaI [J] . Chem J Chinese U，2014, 35(3):538-549. doi:10. 7503/cjcu20130646
  • [31] FANG C, LU T, ZHU J, et al. Formal [3+4] Annulation of Alpha, Beta-unsaturated Acyl Azoliums: Access to Enantioenriched N—H-Free 1, 5-benzothiazepines [J] . Org Lett，2017, 19 (13):3470-3473. doi:10. 1021/acs. orglett. 7b01457

版权所有 2013-2021 河北师范大学学报编辑部 地址：河北省石家庄市南二环东路20号

邮编：050024 电话：0311-80786360 技术支持：载驰科技