SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1759 - 1769

DOI: https://doi.org/10.6023/cjoc202111015

研究论文

乙烯基硒盐参与的串联反应合成1-[1-(胺基)环丙基]酮化合物

  • 袁飞 ,
  • 赵艳 ,
  • 郭青松 ,
  • 尹福丹 ,
  • 赖金荣 ,
  • 念倍芳 ,
  • 张明 ,
  • 汤峨
展开
  • 云南大学 教育部自然资源药物化学重点实验室 昆明 650091
† 共同第一作者

收稿日期: 2021-11-07

  修回日期: 2022-02-07

  网络出版日期: 2022-02-25

基金资助

长江学者和创新团队发展计划(IRT17R94); 国家自然科学基金(21762046); 国家自然科学基金(22161050); 云南科技厅-云南大学“双一流”建设联合基金(2018FY001); 云南省高校科技创新团队支持计划及云南大学“青年英才”培育计划资助项目

收起

Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt

  • Fei Yuan ,
  • Yan Zhao ,
  • Qingsong Guo ,
  • Fudan Yin ,
  • Jinrong Lai ,
  • Beifang Nian ,
  • Ming Zhang ,
  • E Tang
Expand
  • Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091
† These authors contributed equally to this work
*E-mail:

Received date: 2021-11-07

  Revised date: 2022-02-07

  Online published: 2022-02-25

Supported by

Program for Changjiang Scholars and Innovative Research Team in University(IRT17R94); Natural Science Foundation of China(21762046); Natural Science Foundation of China(22161050); Program for Yunnan Provincial Department of Science and Technology-Yunnan University "Double First-Class" Construction Joint Fund(2018FY001); Innovative Research Team(in Science and Technology) in University of Yunnan Province and the Program for the “Young Talent” in Yunnan University

Fold

摘要

发展了一种“一锅法”高效合成1-[1-(胺基)环丙基]酮化合物的新方法. 在碱的作用下, β-胺基酮化合物与甲基苯基乙烯基硒四氟硼酸盐发生亲核加成/质子转移/亲核取代脱硒醚的串联反应, 以70%~93%的产率得到1-[1-(胺基)环丙基]酮化合物. 该方法具有条件温和、操作简单、官能团兼容性良好、区域选择性好等优点. 用溴素和肼对副产物甲基苯基硒醚与乙烯基硒盐进行简单处理, 就可以制备出合成硒盐的通用原料二苯基二硒醚, 继而实现乙烯基硒盐的再生和重复利用, 大大地提高了高价硒试剂的利用效率和该方法的工业应用价值.

关键词： 高价硒试剂; 1-[1-(胺基)环丙基]酮; 一锅法; 串联反应

本文引用格式

袁飞 , 赵艳 , 郭青松 , 尹福丹 , 赖金荣 , 念倍芳 , 张明 , 汤峨 . 乙烯基硒盐参与的串联反应合成1-[1-(胺基)环丙基]酮化合物[J]. 有机化学, 2022 , 42(6) : 1759 -1769 . DOI: 10.6023/cjoc202111015

Abstract

A new one-pot method for the efficient synthesis of 1-(1-(amino)cyclopropyl)ketone compounds has been developed. Under the mediation of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1-(1-(amino)cyclopropyl)ketones were obtained in 70%~93% yields through a reaction sequence of nucleophilic addition/proton migration/nucleophilic substitution and deselenization of β-amino ketones and methyl phenyl vinyl selenium tetrafluoroborate. This method features mild reaction conditions, simple experiment operation, good functional group compatibility. Diphenyl diselenide, the general substrate of the selenium salt reagents, can be prepared by the simple treatment of the by-product methyl phenyl selenide with bromine and hydrazine. Therefore, the vinylselenide salts can be regenerated and reused, which improves the utilization of high-valent selenium reagents and improves the industrial application of this method.

Key words： high valent selenium salt; 1-(1-(amino)cyclopropyl)ketones; one-pot method; tandem reaction

参考文献

[1]
(a) Liu, H.-W.; Walsh, C. T. The Chemistry of the Cyclopropyl Group, Ed.: Rappoport, Z., John Wiley & Sons Ltd., New York, 1987.
[1]
(b) Wessjohann, L. A.; Brandt, W. Chem. Rev. 2003, 103, 1625.
[2]
Wan, L.-Z.; Wang, H. Chemistry (Huaxue Tongbao) 2019, 82, 963. (in Chinese)
[2]
( 万灵子, 王晗, 化学通报, 2019, 82, 963.)
[3]
(a) Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
[3]
(b) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
[3]
(c) Cohen, Y.; Cohen, A.; Marek, I. Chem. Rev. 2021, 121, 140.
[3]
(d) Ebner, C.; Carreira, E. M. Chem. Rev. 2017, 117, 11651.
[3]
(e) Pirenne, V.; Muriel, B.; Waser, J. Chem. Rev. 2021, 121, 227.
[4]
(a) Barone, V.; Fraternali, F.; Cristinziano, P. L.; Lelj, F.; Rosa, A. Biopolymers 1988, 27, 1673.
[4]
(b) Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Crisma, M.; Valle, G.; Toniolo, C. Biopolymers 1989, 28, 175.
[4]
(c) Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287.
[4]
(d) Burgess, K.; Ke, C. Y. J. Pept. Res. 1997, 49, 201.
[5]
(a) Burgess, K.; Li, W.; Lim, D.; Moye-Sherman, D. Biopolymers 1997, 42, 439.
[5]
(b) Martin, S. F.; Dwyer, M. P.; Hartmann, B.; Knight, K. S. J. Org. Chem. 2000, 65, 1305
[5]
(c) Davidson, J. P.; Lubman, O.; Rose, T.; Waksman, G.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 205.
[6]
(a) Ner, S. K.; Suckling, C. J.; Bell, A. R.; Wrigglesworth, R. Chem. Commun. 1987, 480.
[6]
(b) Kemp, A.; Tedford, C.; Suckling, C. J. Bioorg. Med. Chem. Lett. 1991, 1, 557.
[6]
(c) Hilier, M. C.; Davidson, J. P.; Martin, S. F. J. Org. Chem. 2001, 66, 1657.
[7]
Andrew, M.; Dominique, G. Nat. Prod. Res. 2005, 19, 639.
[8]
Talele, T. T. J. Med. Chem. 2016, 59, 8712.
[9]
(a) Han, W.; Hu, Z.; Jiang, X.; Wasserman, Z. R.; Decicco, C. P. Bioorg. Med. Chem. Lett. 2003, 13, 1111.
[9]
(b) Lamarre, D.; Anderson, P. C.; Bailey, M.; Beaulieu, P.; Bolger, G.; Bonneau, P.; Bos, M.; Cameron, D. R.; Cariter, M.; Cordingley, M. G.; Faucher, A.-M.; Goudreau, N.; Kawai, S. H.; Kukolj, G.; Lagace, L.; Laplante, S. R.; Narjes, H.; Poupart, M.-A.; Rancourt, J.; Sentjens, R. E.; St George, R.; Simoneau, B.; Steinmann, G.; Thiebeault, D.; Tsantrizos, Y. S.; Weldon, S. M.; Yong, C.-L.; Llinas-Brunet, M. Nature 2003, 426, 186.
[10]
Kawada, M.; Kawano, Y.; Sugihara, H.; Takei, S.; Imada, I. Chem. Pharm. Bull. 1981, 29, 1900.
[11]
Brotherton, C. A.; Wilson, M.; Byrd, G.; Balskus, E. P. Org. Lett. 2015, 17, 1545.
[12]
Serusi, L.; Soddu, F.; Cuccu, F.; Peretti, G.; Luridiana, A.; Secci, F.; Caboni, P.; Aitken, D. J.; Frongia, A. Adv. Synth. Catal. 2020, 362, 4159.
[13]
Mao, Z.-J.; Qu, H.-J.; Zhao, Y.-Y.; Lin, X.-F. Chem. Commun. 2012, 48, 9927.
[14]
Wirth, T. Organoselenium Chemistry (Synthesis and Reactions), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2012, pp. 204-211.
[15]
(a) Tang, E; Wang, W. L.; Zhao, Y. J.; Zhang, M.; Dai, X. Org. Lett. 2016, 18, 176.
[15]
(b) Tang, E; Zhao, Y. J.; Li, W.; Wang, W. L.; Zhang, M.; Dai, X. Org. Lett. 2016, 18, 912.
[15]
(c) Tang, E; Zhao, Y. J.; Zhang, M.; Dai, X.; Wang, W. L. Heterocycles 2016, 92, 708.
[15]
(d) Sun, Q.; Liao, M. H.; Zhao, Y.; Li, Y. X.; Liu, S. S.; Mao, D. S.; Tang, E. Heterocycles 2019, 98, 1563.
[15]
(e) Liao, M. H.; Zhang, M.; Hu, D. H.; Zhang, R. H.; Zhao, Y.; Liu, S. S.; Li, Y. X.; Xiao, W. L.; Tang, E Org. Biomol. Chem. 2020, 18, 3941.
[16]
(a) Tang, Y.; Ye, S.; Sun, X.-L. Synlett 2005, 2720.
[16]
(b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
[16]
(c) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87.
[16]
(d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
[17]
Watanabe, S.-I.; Kusumoto, T.; Yoshida, C.; Kataoka, T. Chem. Commun. 2001, 839.
[18]
(a) Borzecka, W.; Lavandera, I.; Gotor, V. J. Org. Chem. 2013, 78, 7312.
[18]
(b) Pal, M.; Swamy, N. K.; Hameed, P. S.; Padakanti, S.; Yeleswarapu, K. R. Tetrahedron 2004, 60, 3987.
[19]
Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042.
[20]
Gilbert, B. B.; Eey, S. T.-C.; Ryabchuk, P.; Garry, O.; Denmark, S. E. Tetrahedron 2019, 75, 4086.
[21]
(a) Mato, M.; Franchino, A.; Garcı?a-Morales, C.; Echavarren, A. M. Chem. Rev. 2021, 121, 8613.
[21]
(b) Gao, J.-S.; Bian, Q.-H.; Guo, H.-C. Chin. J. Org. Chem. 2007, 27, 438. (in Chinese)
[21]
( 高金山, 边庆花, 郭洪超, 有机化学, 2007, 27, 438.)
[21]
(c) Liang, J.; Ma, H.-F.; Ablajan, K. Chin. J. Org. Chem. 2019, 39, 3169. (in Chinese)
[21]
( 梁杰, 马会芳, 阿布拉江•克依木, 有机化学, 2019, 39, 3169.)
[21]
(d) Wang, M.; Chen, J.; Wu, X.-Y.; Deng, H.-M.; Zhang, H.; Shao, M.; Cao, W.-G. Chin. J. Org. Chem. 2009, 29, 1611. (in Chinese)
[21]
( 王猛, 陈杰, 吴小余, 邓红梅, 张慧, 邵敏, 曹卫国, 有机化学, 2009, 29, 1611.)
[21]
(e) Su, G.-F.; Pan, C.-X.; Mou, H.-T.; Zeng, L.-M.; Yu, K.-B. Acta Chim. Sinica 2004, 62, 1941. (in Chinese)
[21]
( 苏桂发, 潘成学, 牟红涛, 曾陇梅, 郁开北, 化学学报, 2004, 62, 1941.)
[21]
(f) Shi, Z.-J.; Liu, M.; Liang, C. Chin. J. Synth. Chem. 2008, 16, 546. (in Chinese)
[21]
( 施志坚, 刘梅, 梁超, 合成化学, 2008, 16, 546.)
[21]
(g) Li, X.-D.; Fan, X.-E.; Zhang, G.-Y.; Chen, Q.-H. Chemistry (Huaxue Tongbao) 2005, 68, 209. (in Chinese)
[21]
( 李晓冬, 范雪娥, 张桂英, 陈庆华, 化学通报, 2005, 68, 209.)
[21]
(h) Gao, T.-Y.; Shi, Z.-J.; Cao, W.-G.; Deng, H.-M. Chin. J. Synth. Chem. 2009, 17, 566. (in Chinese)
[21]
( 高天云, 施志坚, 曹卫国, 姜海燕, 邓红梅, 合成化学, 2009, 17, 566.)
[21]
(i) Zhang, X.-L.; Huang, H.-H.; Chen, Q.-H. Chin. J. Org. Chem. 2002, 22, 411. (in Chinese)
[21]
( 张熊禄, 黄海洪, 陈庆华, 有机化学, 2002, 22, 411.)
[21]
(j) Jin, W.-B.; Yuan, H.; Tang, G.-L. Chin. J. Org. Chem. 2018, 38, 2324. (in Chinese)
[21]
( 金文兵, 袁华, 唐功利, 有机化学, 2018, 38, 2324.)
[22]
Luan, B.; Catalina, S.; Lorenzo, T.; Marcello, T. Tetrahedron: Asymmetry 2009, 20, 1506.
[23]
Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042.
[24]
Francesca, G. N.; Bonifacio, M.; Eder, J. L.; Paul, E.; Claudio, S. Molecules 2020, 25, 2018.
[25]
Guo, S.-Q.; Zhang, N.-N.; Tang, X.-Z.; Mao, Z.-F.; Zhang, X.-J.; Yan, M.; Xuan, Y.-N. Chin. Chem. Lett. 2019, 30, 406.
[26]
Mao, Z.-J.; Qu, H.-J.; Zhao, Y.-Y.; Lin, X.-F. Chem. Commun. 2012, 48, 9927.
Options
文章导航

/

〈 〉