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

Chemical Research in Chinese Universities ›› 2006, Vol. 22 ›› Issue (1): 36-39.

• Articles • Previous Articles Next Articles

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

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

Received:2005-05-11 Online:2006-02-24 Published:2011-08-06
Supported by:
Supported partly by the National Natural Science Foundation of China(Nos. 20272002 and 20472005), Ministry of Education of P. R. China(SRF for ROCS and EYTP) and Peking University(President Grant).

Abstract

Abstract: The reactions of 2,3-dihydro-1,5-benzothiazepines with ethoxycarbonylcarbene undergo complex rearrangements to produce ring-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.

Key words: 1,5-Benzothiazepine, Ethoxycarbonylcarbene, Rearrangement, Ring-contraction, Ring-opening

WU Chun-zan, HUANG Jia-xing, ZHANG Qi-han, XU Jia-xi. Further Investigation on the Rearrangement Mechanism of Reactions of 1,5-Benzothiazepines with Ethoxycarbonylcarbene[J]. Chemical Research in Chinese Universities, 2006, 22(1): 36-39.

[1]	WANG Wenyang, LIU Hanlin, YANG Caoyu, FAN Ting, CUI Chengqian, LU Xiaoquan, TANG Zhiyong, LI Guodong. Coordinating Zirconium Nodes in Metal-Organic Framework with Trifluoroacetic Acid for Enhanced Lewis Acid Catalysis [J]. Chemical Research in Chinese Universities, 2022, 38(5): 1301-1307.
[2]	TONG Jie, LIU Chang, WANG Bo. Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A [J]. Chemical Research in Chinese Universities, 2019, 35(5): 817-822.
[3]	WANG Ying, WANG Qiliao, HOU Liman, ZHOU Mingdong, DONG Dewen, ZHANG Ning. Functionalized Polyphosphoester via Living Ring-opening Polymerization and Photochemical Thiol-ene Click Reaction [J]. Chemical Research in Chinese Universities, 2019, 35(2): 340-344.
[4]	QIAO Yaping, YUAN Xiaoyan, ZHAO Yunhui, REN Lixia. Ceiling Degree of Polymerization for Brush Polymers Prepared via ROMP of Poly(tert-Butyl Acrylate) Macromonomers [J]. Chemical Research in Chinese Universities, 2018, 34(5): 828-832.
[5]	Kingsadingthongkham VONGDETH, RAN Liqiong, YAN Lili, WANG Qiuan. Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents [J]. Chemical Research in Chinese Universities, 2018, 34(4): 564-570.
[6]	ZHANG Ran, XU Lihua, CHEN Hui, QIN Zhihong, ZHAO Yu, Ni Zhonghai. Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement [J]. Chemical Research in Chinese Universities, 2015, 31(2): 224-227.
[7]	HAN Yancheng, ZHU Guangyun, ZHANG Mengmeng, WANG Shuai, YAO Wei, GAO Aihong, LU Ping. Synthesis and Characterization of Dinuclear Aluminum Complexes Bearing N,N-Dialkylaniline-amido Ligands and Its Catalytic Properties for Lactone Polymerization [J]. Chemical Research in Chinese Universities, 2014, 30(5): 874-878.
[8]	LIU Tingting, LU Xi, ZHANG Mingtao. Theoretical Exploration of Stereochemical Nonrigidity for R_fCo(PF₃)_x(CO)_4-x(R_f=CF₃, C₂F₅, C₃F₇, x=0-4) [J]. Chemical Research in Chinese Universities, 2014, 30(4): 656-660.
[9]	YAO Wei, XUE Yingzhao, LIU Tiantian, GAO Aihong, WANG Yanfeng. Zinc Complexes Supported by N, N-Dimethylaniline-arylamido Ligands：Synthesis, Characterization and Catalytic Properties for Ring-opening Polymerization of L-Lactide [J]. Chemical Research in Chinese Universities, 2014, 30(1): 87-90.
[10]	XU Qing-hui, LI Ji-zhen, HE Jiang-hua, ZHAO Xin, HUO Qi-sheng. Synthesis of Novel Flavanone Derivatives and Their Anti Staphylococcus aureus Evaluation [J]. Chemical Research in Chinese Universities, 2013, 29(4): 695-698.
[11]	WEI Ying, LI Xiao-yuan, JING Xia-bin, CHEN Xue-si, HUANG Yu-bin. Preparation of Poly(serine ester)s by Ring-opening Polymerization of N-Trityl Serine Lactone Under Catalysis of ZnEt₂ [J]. Chemical Research in Chinese Universities, 2013, 29(1): 177-182.
[12]	YAO Wei, CUI Ning, XUE Ying-zhao, LIU Tian-tian, WANG Yan. Anilido-imine Zinc Complexes: Efficient Catalysts for Ring-opening Polymerization of L-Lactide [J]. Chemical Research in Chinese Universities, 2013, 29(1): 48-50.
[13]	WU Mao-cheng, DUAN Hai-feng*, CAO Jun-gang, LIANG Da-peng, JIANG Feng, GAO Han, JIA Xu-dong and LIN Ying-jie. BrΦnsted Acidic Ionic Liquids: Efficient and Recyclable Catalytic Systems for Beckmann Rearrangement [J]. Chemical Research in Chinese Universities, 2011, 27(6): 973-976.
[14]	ZHANG Lan-ping and WANG Ya-lou*. Facile Synthesis of 5-Hydroxy-2-(2-phenylethyl)chromone [J]. Chemical Research in Chinese Universities, 2010, 26(2): 245-248.
[15]	ZHAO Xi, LI Bin, XU Shan-sheng, SONG Hai-bin and WANG Bai-quan* . Synthesis, Structure, and Ring-opening Metathesis Polymerization of η⁵-Pentamethylcyclopentadienyl-(η⁵-exo-tricyclo[5.2.1.0^2,6]deca-2,5,8-trien-6-yl) Iron [J]. Chemical Research in Chinese Universities, 2009, 25(5): 662-665.

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

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments