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2020 , Vol. 40 >Issue 3: 694 - 703

DOI: https://doi.org/10.6023/cjoc201909009

研究论文

无催化剂条件下4-羟基烷基-2-炔酸乙酯与N-杂环芳基甲基-N-2,2-二氟乙基-1-胺的串联反应

  • 赵宇 ,
  • 王卫伟 ,
  • 刘鑫磊 ,
  • 耿瑞 ,
  • 王明安
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  • 中国农业大学应用化学系 北京 100193

收稿日期: 2019-09-06

  修回日期: 2019-10-11

  网络出版日期: 2019-11-07

基金资助

国家自然科学基金（No.21772229）资助项目.

收起

Catalyst-Free Domino Reaction of Ethyl 4-Hydroxyalkyl-2-ynoate with N-Heteroarylmethyl-N-2,2-difluoroethan-1-amine

  • Zhao Yu ,
  • Wang Weiwei ,
  • Liu Xinlei ,
  • Geng Rui ,
  • Wang Ming'an
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  • Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2019-09-06

  Revised date: 2019-10-11

  Online published: 2019-11-07

Supported by

Project supported by the National Natural Science Foundation of China (No. 21772229).

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摘要

开发了无催化剂条件下4-羟基烷基-2-炔酸乙酯与N-杂环芳基甲基-N-2，2-二氟乙基-1-胺的串联反应.应用该反应在甲醇中回流，以39%～83%的收率合成了一系列4-（N-（2，2-二氟乙基）（N-杂环芳基甲基）氨基）-5，5-二取代呋喃-2（5H）-酮，其结构经1H NMR，13C NMR和HR-ESI-MS表征，并进一步通过3-氯-4-（（N-2，2-二氟乙基）（N-嘧啶-5-基甲基胺基）-5，5-螺（4-甲氧基环己基）呋喃-2（5H）-酮（8）的晶体衍射间接证实.测试了所合成化合物的生物活性，结果表明，在600 μg·mL－1浓度时4-（（N-2，2-二氟乙基）（N-6-氯吡啶-3-基甲基胺基）-5，5-二甲基呋喃-2（5H）-酮（3a）和4-（（N-2，2-二氟乙基）（N-6-氟吡啶-3-基甲基胺基）-5，5-二甲基呋喃-2（5H）-酮（3c）对桃蚜的死亡率均为100%.

关键词： 5,5-二取代呋喃-2(5H)-酮; 串联反应; 加成-内酯化反应; 杀虫活性

本文引用格式

赵宇 , 王卫伟 , 刘鑫磊 , 耿瑞 , 王明安 . 无催化剂条件下4-羟基烷基-2-炔酸乙酯与N-杂环芳基甲基-N-2,2-二氟乙基-1-胺的串联反应[J]. 有机化学, 2020 , 40(3) : 694 -703 . DOI: 10.6023/cjoc201909009

Abstract

The catalyst-free domino reaction of ethyl 4-hydroxyalkyl-2-ynoate and N-heteroaryl-methyl-N-2,2-difluoroethan-1-amine was developed, and used to synthesize 4-(N-(2,2-difluoroethyl)(N-heteroarylmethyl)amino)-5,5-disubstitutedfuran-2(5H)-one in methanol under the reflux condition with yields of 39%~83%. Their structures were characterized by 1H NMR, 13C NMR, and HR-ESI-MS data, further confirmed by the X-ray crystal diffraction of 3-chloro-4-((N-2,2-difluoroethyl)(N-pyrimidin-5-ylmethyl)amino)-5,5-spiro(4-methoxycyclohexyl)furan-2(5H)-one (8). The bioassay results showed that 4-((N-2,2-difluoroethyl)(N-6-chloropyridin-3-ylmethyl)amino)-5,5-dimethylfuran-2(5H)-one (3a) and 4-((N-2,2-difluoroethyl)(N-6-fluoropyridin-3-ylmethyl)-amino)-5,5-dimethylfuran-2(5H)-one (3c) exhibit 100% mortality against Myzus persicae at the concentration of 600 μg·mL-1, respectively.

Key words： 5,5-disubstitutedfuran-2(5H)-one; domino reaction; addition-lactonization; insecticidal activity

参考文献

[1] (a) Rao, Y. S. Chem. Rev. 1976, 76, 625.
(b) Allan, R. D.; Johnston, G. A. R.; Kazlauskas, R.; Tran, H. W. J. Chem. Soc., Perkin Trans. 1 1983, 2983.
(c) Gelmi, M. L.; Clerici, F.; Melis, A. Tetrahedron 1997, 53, 1843.
(d) Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 136, 16477.
[2] (a) Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-kintscher, U.; Thielert, W.; Wolfel, K.; Hass, M.; Kunz, K.; Raupach, G. Pest Manage. Sci. 2015, 71, 850.
(b) Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem. 2016, 24, 317.
(c) Chen, X. D.; Seo, M.; Stelinski, L. L. Crop Prot. 2017, 98, 102.
(d) Roditakis, E.; Stavrakaki, M.; Grispou, M.; Achimastou, A.; Waetermeulen, X. V.; Nauen, R.; Tsagkarakou, A. Pest Manage. Sci. 2017, 73, 1574.
[3] (a) Murakami, T.; Morikawa, Y.; Hashimoto, M.; Okuno, T.; Harada, Y. Org. Lett. 2004, 6, 157.
(b) Nomiya, M.; Murakami, T.; Takada, N.; Okuno, T.; Harada, Y.; Hashimoto, M. J. Org. Chem. 2008, 73, 5039.
(c) Lachia, M. D.; Demesaeker, A.; Wolf, H. C.; Jung, P. J. M. WO 2012080115, 2012.
(d) Liu, M.; Lin, S.; Gan, M.; Chen, M.; Li, L.; Wang, S.; Zi, J. Org. Lett. 2012, 14, 1004.
[4] (a) Liu, T.-X. Crop Prot. 2004, 23, 505.
(b) Nauen, R.; Bretschneider, T.; Elbert, A.; Fischer, R.; Tiemann, R. Pestc. Outlook 2003, 243.
[5] (a) Jeschke, P.; Nauen, R.; Gutbrot, O.; Beck, M. E.; Matthiesen, S.; Hass, M.; Velten, R. Pestic. Biochem. Physiol. 2015, 121, 31.
(b) Fan, Z. J.; Zong, G. N.; Ma, L. Y.; Chen, L.; Guo, X. F. CN 105503708, 2016.
(c) Tian, P. Y.; Liu, D. Y.; Liu, Z. J.; Shi, J.; He, W. J.; Qi, P. Y.; Chen, J. X.; Song, B. A. Pest Manage. Sci. 2019, 75, 427.
[6] (a) Fischer, R.; Himmler, T.; Nauen, R.; Reckmann, U.; Schmitt, W. In Proceedings of the International Plant Protection Congress, International Plant Protection Congress, Glasgow, 2007, pp. 100～103.
(b) Zhao, J. H.; Ji, M. H.; Xu, X. H.; Cheng, J. L.; Zhu, G. N. Chin. Chem. Lett. 2009, 20, 1307.
(c) Song, F. J.; Liu, Y. H. J. Organomet. Chem. 2014, 694, 502.
(d) Melikyan, G. S.; Hovhannisyan, A. A.; Hayotsyan, S. S. Synth. Commun. 2012, 42, 2267.
(e) Muehlebach, M.; Boeger, M.; Cederbaum, F.; Cornes, D.; Friedmann, A. A.; Glock, J.; Niderman, T.; Stoller, A.; Wagner, T. Bioorg. Med. Chem. 2009, 17, 4241.
(f) Liu, Z. H.; Lei, Q.; Li, Y. Q.; Xiong, L. X.; Song, H. B.; Wang, Q. M. J. Agric. Food Chem. 2011, 59, 12543.
[7] (a) Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A.; Zhou, L. G. Chin. J. Chem. 2017, 35, 1133.
(b) Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663.
(c) Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740.
[8] Zhao, Y.; Liu, X. L.; Wang, W. W.; Geng, R.; Wang, M. A. Synthesis 2018, 50, 4055.
[9] (a) Arkadi, A.; Bernocchi, E.; Burini, A.; Cacchi, S.; Marinelli, F.; Pietroni, B. Tetrahedron 1988, 44, 481.
(b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
(c) Oh, C. H.; Park, S. J.; Ryu, J. H.; Gupta, A. K. Tetrahedron Lett. 2004, 45, 7039.
(d) Alfonsi, M.; Arkadi, A.; Chiarini, M.; Marinelli, F. J. Org. Chem. 2007, 72, 9510.
(e) Zhou, L.-H.; Yu, X.-Q.; Pu, L. J. Org. Chem. 2009, 74, 2103.
(f) Ramon, R. S.; Pottier, C.; Gomez-Suarez, A.; Nolan, S. P. Adv. Synth. Catal. 2011, 353, 1575.
(g) Yamamoto, Y.; Shibano, S.; Kurohara, T.; Shibuya, M. J. Org. Chem. 2014, 79, 4503.
[10] (a) Peter, J.; Robert, V.; Thomas, S.; Otto, S.; Michael, B. DE 102006015467, 2007.
(b) Lui, N.; Heinrich, J.-D. US 20110152534, 2011.
(c) Zhao, Y.; Tang, B.; Liu, X. L.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 957(in Chinese). (赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安, 有机化学, 2017, 37, 957.)
(d) Zhao, Y.; Guan, A. Y.; Li, W. Z.; Wang, W. W.; Liu, X. L.; Wang, M. A. Chin. J. Org. Chem. 2019, 39, 1344(in Chinese). (赵宇, 关爱莹, 李婉祯, 王卫伟, 刘鑫磊, 王明安, 有机化学, 2019, 39, 1344.)
[11] (a) Ogawa, A. K.; Willoughby, C. A.; Bergeron, R.; Ellsworth, K. P.; Geissler, W. M.; Myers, R. W.; Yao, J.; Harries, G.; Chapman, K. T. Bioorg. Med. Chem. Lett. 2003, 13, 3405.
(b) Chouldhary, G.; Peddinti, R. K. Green Chem. 2011, 13, 3290.
(c) Wang, Z.; Wang, M.; Yao, X.; Li, Y.; Tan, J.; Wang, L.; Qiao, W.; Geng, Y.; Liu, Y.; Wang, Q. Eur. J. Med. Chem. 2012, 54, 33.
[12] Arcadi, A.; Alfonsi, M.; Marinelli, F. Tetrahedron Lett. 2009, 50, 2060.
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