“Hofmann-Löffler-Freytag”型反应合成吡咯烷类化合物的研究进展

doi:10.3866/PKU.DXHX202006030

Abstract

Abstract:

Nitrogen-containing heterocycles exist widely in natural products, pharmaceuticals and optical materials. These molecules often exhibit high levels of biological and optical activities. Especially, the pyrrolidine derivatives are privileged structural units existed in natural products and pharmaceuticals. Therefore, the development of efficient methods to construct this ubiquitous structure unit is highly desirable. This paper introduces the development of Hofmann-Löffler-Freytag (HLF) reaction in synthesis of pyrrolidine derivatives. The major contents are including two aspects: 1) Halogen-mediated HLF reactions; 2) Non halogen-mediated HLF reactions.

Key words: Hofmann-Löffler-Freytag type reaction, Pyriolidine derivatives, Halogen-mediated, Non halogen-mediated

MSC2000:

Mingyu Yang. Progress in Synthesis of Pyrrolidine Derivatives by Hofmann-Löffler-Freytag Type Reactions[J].University Chemistry, 2021, 36(6): 2006030.

Figures/Tables 17

References 35

1	Jeffrey J. L. ; Sarpong R. Chem. Sci. 2013, 4, 4092. doi: 10.1039/c3sc51420j
2	Yuan J. ; Liu C. ; Lei A. Chem. Commun. 2015, 51, 1394. doi: 10.1039/C4CC08116A
3	Park Y. ; Kim Y. ; Chang S. Chem. Rev. 2017, 117 (13), 9247. doi: 10.1021/acs.chemrev.6b00644
4	Vitaku E. ; Smith D. T. ; Njardarson J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b
5	Wei J. ; Han B. ; Guo Q. ; Shi X. ; Wang W. ; Wei N. Angew. Chem. Int. Ed. 2010, 49, 8209. doi: 10.1002/anie.201002369
6	Steele J. C. P. ; Veitch N. C. ; Kite G. C. ; Simmonds S. J. M. ; Warhurst D. C. J. Nat. Prod. 2002, 65, 85. doi: 10.1021/np0101705
7	Nicolaou K. C. ; Dalby S. M. ; Majumder U. J. Am. Chem. Soc. 2008, 130, 14942. doi: 10.1021/ja806176w
8	Türkmen Y. E. ; Gravel M. ; Rawal V. H. J. Org. Chem. 2016, 81, 10454. doi: 10.1021/acs.joc.6b01574
9	Mori M. ; Kuroda S. ; Zhang C.-S. ; Sato Y. J. Org. Chem. 1997, 62, 3263. doi: 10.1021/jo9701187
10	Hofmann A. W. Ber. Dtsch. Chem. Ges. 1879, 12, 984. doi: 10.1002/cber.187901201254
11	Hofmann A. W. Ber. Dtsch. Chem. Ges. 1881, 14, 2725. doi: 10.1002/cber.188101402242
12	Hofmann A. W. Ber. Dtsch. Chem. Ges. 1883, 16, 558. doi: 10.1002/cber.188301601120
13	Hofmann A. W. Ber. Dtsch. Chem. Ges. 1885, 18, 5. doi: 10.1002/cber.18850180103
14	Hofmann A. W. Ber. Dtsch. Chem. Ges. 1885, 18, 109. doi: 10.1002/cber.18850180126
15	Löffler K. Ber. Dtsch. Chem. Ges. 1910, 43, 2035. doi: 10.1002/cber.191004302146
16	Löffler K. ; Freytag C. Ber. Dtsch. Chem. Ges. 1909, 42, 3427. doi: 10.1002/cber.19090420377
17	Löffler K. ; Kaim H. Ber. Dtsch. Chem. Ges. 1909, 42, 94. doi: 10.1002/cber.19090420112
18	Löffler K. ; Kober S. Ber. Dtsch. Chem. Ges. 1909, 42, 3431. doi: 10.1002/cber.19090420378
19	Wolff M. E. Chem. Rev. 1963, 63, 55. doi: 10.1021/cr60221a004
20	Betancor C. ; Concepcion J. I. ; Hernandez R. ; Salazar. J. A. ; Suárez E. J. Org. Chem. 1983, 48, 4430. doi: 10.1021/jo00171a066
21	Carrau R. ; Hernández R. ; Suárez E. ; Betancor C. J. Chem. Soc., Perkin Trans. 1 1987, 937.
22	Francisco C. G. ; Herrera A. J. ; Suárez E. J. Org. Chem. 2003, 68, 1012. doi: 10.1021/jo026314h
23	Hernández R. ; Rivera A. ; Salazar A. ; Suárez E. J. Chem. Soc. Chem. Commun. 1980, 958
24	Fan R. ; Pu D. ; Wen F. ; Wu J. J. Org. Chem. 2007, 72, 8994. doi: 10.1021/jo7016982
25	Paz N. R. ; Rodíguez-Sosa D. ; Valdés H. ; Marticorena R. ; Melián D. ; Copano M. B. ; González C. C. ; Herrera A. J. Org. Lett. 2015, 17, 2370. doi: 10.1021/acs.orglett.5b00866
26	Martínez C. ; Muñiz K. Angew. Chem. Int. Ed. 2015, 54, 8287. doi: 10.1002/anie.201501122
27	Duhamel T. ; Stein C. J. ; Martínez C. ; Reiher M. ; Muñiz K. ACS Catal. 2018, 8, 3918. doi: 10.1021/acscatal.8b00286
28	Castillo E. D. ; Muñiz K. Org. Lett. 2019, 21, 705. doi: 10.1021/acs.orglett.8b03909
29	Qin Q. ; Yu S. Org. Lett. 2015, 17, 1894. doi: 10.1021/acs.orglett.5b00582
30	O'Broin C. Q. ; Fernández P. ; Martínez C. ; Muñiz K. Org. Lett. 2016, 18, 436. doi: 10.1021/acs.orglett.5b03476
31	Bafaluy D. ; Muñoz-Molina J. M. ; Funes-Ardoiz I. ; Herold S. ; de Aguirre A. J. ; Zhang H. ; Maseras F. ; Belderrain T. ; Pérez P. J. ; Muñiz K. Angew. Chem. Int. Ed. 2019, 58, 8912. doi: 10.1002/anie.201902716
32	Wappes E. A. ; Fosu S. C. ; Chopko T. C. ; Nagib D. A. Angew. Chem. Int. Ed. 2016, 55, 9974. doi: 10.1002/anie.201604704
33	Becker P. ; Duhamel T. ; Martínez C. ; Muñiz K. Angew. Chem. Int. Ed. 2018, 57, 5166. doi: 10.1002/anie.201800375
34	Nikishin G. I. ; Troyansky E. I. ; Lazareva M. I. Tetrahedron 1985, 41, 4279. doi: 10.1016/S0040-4020(01)97199-6
35	Meng D. ; Tang Y. ; Wei J. ; Shi X. ; Yang M. Chem. Commun. 2017, 53, 5744. doi: 10.1039/C7CC02624B

[1]	Zhuping Xiao, Qiuju Feng. Application of Electronic Density Distribution Analysis in Organic Chemistry Teaching for Developing Organic Chemistry Thinking [J]. University Chemistry, 0, (): 2106046-.
[2]	Qingwang Xue, Shuling Xu, Yuanfu Zhang, Debin Huang, Aifeng Li, Xia Li, Huaisheng Wang. Exploration on the Experimental Teaching Mode Based on Scientific Research Penetration from the Perspective of Ideological and Political Courses [J]. University Chemistry, 0, (): 2107046-.
[3]	Ningning Dong, Linqi Xu, Feng Xiong, Boyu Yan, Kun Li, Dongcai Guo. Design of a Comprehensive Experiment: Titanium Carbide MXenes Mediated In Situ Reduction for Label-Free and Visualized Sensing of Silver Ions [J]. University Chemistry, 0, (): 2111060-.
[4]	Hongwei Zhao, Jiameng Huai, Ze Wang, Xia Chen. Complexometric Titration for the Determination of Zno in Pharmaceutical Preparations: Application of Quantitative Chemical Analysis in Practice [J]. University Chemistry, 0, (): 2111067-.
[5]	Zhixiang Yao, Xin Ma, Jingqing Zhang, Yuting Su, Hui Su. Laboratory Teaching Practice of On-Line Analysis of Aspirin Synthesis Process [J]. University Chemistry, 0, (): 2111076-.
[6]	Jianghua Li, Juntao Tang, Mei Mei, Wansong Chen, Limiao Chen, Fa Zhou, Jianhan Huang, Younian Liu. Preparation and Flame Retardancy Test of Ammonium Polyphosphate: A Comprehensive Applied Chemistry Experiment [J]. University Chemistry, 0, (): 2112001-.
[7]	Lihua Jin, Lei Tian, Chaozhan Wang, Yan Li, Yanli Guo, Hongfang Zhang. The Application Exploitation of Integrating Mind-Mapping into TaskDriven Teaching Method in Analytical Chemistry Course [J]. University Chemistry, 0, (): 2112042-.
[8]	Peijuan Zhang, Bo Zhao, Fengyi He, Hanfei Luo, Qifei Shen, Dongfeng Dang. The Comprehensive Innovation Experiment for Undergraduate: Study on Aggregation-Induced Emission of Tetraphenylethylene and the Application in Fingerprint Imaging [J]. University Chemistry, 0, (): 2112045-.
[9]	Xiaoyan Li, Huaiyu Zhang, Lingpeng Meng, Yanli Zeng. Exploration and Practice of Mixed Online/Offline Teaching in Computational Chemistry Laboratory [J]. University Chemistry, 0, (): 2112054-.
[10]	Yuanfei Li, Xunfang Yang, Guiling Wang, Ying Guo, Xu Wang, Xinru Li, Yanxia Zhou, Ying Xie. Determination of Surface Tension Isotherm of Phospholipid Solution Using Wilhelmy Method [J]. University Chemistry, 0, (): 2201014-.
[11]	Yu Zhang, Tingting Ji, Xinyan Zhang, Chunhao Li, Shuai Wang. Comprehensive Experimental Design of Organic Chemistry Based on Scientific Research Infiltration: Preparation of an Anti-Counterfeiting Ink [J]. University Chemistry, 0, (): 2111080-.
[12]	Ya Wu, Rongmiao Fang, Dan Xue, Wenzhen Wang, Yefei Nan, Biyun Su, Jun Shi. Exploration and Practice of Chemistry Laboratory Skill Competition in Collaboration with Traditional Laboratory Teaching [J]. University Chemistry, 0, (): 2111083-.
[13]	Nan Zhang, Jianyang Zang, Gang Wang, Taihong Liu. Nonlinear Characterization and Related Photophysics of Two-Photon Absorption [J]. University Chemistry, 0, (): 2201037-.
[14]	Liang Shi, Honglan Qi, Lu Zhang, Chengxiao Zhang. Discussion on the Definition and Improving Strategies of Selectivity in Analytical Chemistry [J]. University Chemistry, 0, (): 2111012-.
[15]	Xiaoyun Hu, Ling Ma, Xinran Yin, Dan Chen, Zhongqiang Zhou, Daohong Zhang. Synthesis and Characterization of (2R,3R)-1,4-Dimethoxyl-1,1,4,4- tetraphenyl-2,3-butanediol: A Recommended Comprehensive Chemistry Experiment [J]. University Chemistry, 0, (): 2111036-.

Progress in Synthesis of Pyrrolidine Derivatives by Hofmann-Löffler-Freytag Type Reactions

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 17

References 35

Related Articles 15

Metrics

Recommended 0