综述与进展

炔丙醇类化合物参与的环化反应研究进展

  • 赵晓正 ,
  • 凌琴琴 ,
  • 曹桂妍 ,
  • 火星 ,
  • 赵小龙 ,
  • 苏瀛鹏
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  • a 西北师范大学化学化工学院 兰州 730030
    b 兰州大学化学化工学院 兰州 730000

收稿日期: 2022-03-20

  修回日期: 2022-06-12

  网络出版日期: 2022-06-23

基金资助

国家自然科学基金(21961034); 国家自然科学基金(21502154); 国家自然科学基金(21362033); 甘肃省科技计划(21JR1RA232); 甘肃省高等学校产业支撑计划(2021CYZC-17)

Research Progress in the Cyclization Reactions with Propargyl Alcohols

  • Xiaozheng Zhao ,
  • Qinqin Ling ,
  • Guiyan Cao ,
  • Xing Huo ,
  • Xiaolong Zhao ,
  • Yingpeng Su
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  • a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
    b College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
* Corresponding author. E-mail:

Received date: 2022-03-20

  Revised date: 2022-06-12

  Online published: 2022-06-23

Supported by

National Natural Science Foundation of China(21961034); National Natural Science Foundation of China(21502154); National Natural Science Foundation of China(21362033); Gansu Provincial Science and Technology Program(21JR1RA232); Industrial Support Program of Gansu Province for Colleges(2021CYZC-17)

摘要

炔丙醇是一类具有醇羟基和碳碳叁键官能团的化合物. 由于该类化合物的特殊结构, 使其显示出独特的反应特性, 并可通过活化其醇羟基或叁键进而参与反应. 最为典型的是它们可与各类化合物发生多种形式的环化反应, 实现了种类繁多的环状化合物制备, 如环戊烯、吡咯、呋喃、环状碳酸酯、吡喃、吡啶和氮杂䓬类环状化合物. 综述了近年来炔丙醇类化合物参与的[3+2]、[2+3]、[3+3]、[4+2]、[2+4]、[4+1]、[3+4]和其它类型的环化反应.

本文引用格式

赵晓正 , 凌琴琴 , 曹桂妍 , 火星 , 赵小龙 , 苏瀛鹏 . 炔丙醇类化合物参与的环化反应研究进展[J]. 有机化学, 2022 , 42(9) : 2605 -2639 . DOI: 10.6023/cjoc202203037

Abstract

Propargyl alcohols as a classical bifunctional group compounds possess alcohol hydroxyl group and carbon-carbon triple bond. Due to their special structure, they show unique reaction characteristics, and are employed in reactions via activating its alcoholic hydroxyl group or triple bond. The most typical reaction for propargyl alcohols is various cyclization reactions with different compounds to assemble a richer variety of cyclized compounds such as cyclopentene, pyrrole, furan, cyclic carbonate, pyran, pyridine and azepine cyclic compounds. The recent research progress in the cyclization reaction of propargyl alcohols with various compounds, including [3+2], [2+3], [3+3], [4+2], [2+4], [4+1], [3+4] and other types of cyclization reactions, is summarized.

参考文献

[1]
(a) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208.
[1]
(b) Xu, W.; Zhao, S.; Luo, X.; Song, J.; Liu, J.; Bi, X.; Liao, P. Chin. J. Org. Chem. 2015, 35, 2095. (in Chinese)
[1]
(徐文帅, 赵寿经, 骆晓沛, 宋金娜, 刘建全, 毕锡合, 廖沛球, 有机化学, 2015, 35, 2095.)
[2]
(a) Garayalde, D.; Nevado, C. ACS Catal. 2012, 2, 1462.
[2]
(b) Kazem Shiroodi, R.; Gevorgyan, V. Chem. Soc. Rev. 2013, 42, 4991.
[2]
(c) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448.
[2]
(d) Zhang, X.; Lü, C.; Li, P.; Fu, B.; Yao, W. Chin. J. Org. Chem. 2016, 36, 1287. (in Chinese)
[2]
(张小祥, 吕昌, 李萍, 付博, 姚薇薇, 有机化学, 2016, 36, 1287.)
[3]
(a) Bi, X.; Zhang, L.; Fang, G.; Kumar, R. Synthesis 2015, 47, 2317.
[3]
(b) Chan, P.; Ayers, B. Synlett 2015, 26, 1305.
[3]
(c) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
[3]
(d) Zhu, Y.; Sun, L.; Lu, P.; Wang, Y. ACS Catal. 2014, 4, 1911.
[4]
Qian, H.; Huang, D.; Bi, Y.; Yan, G. Adv. Synth. Catal. 2019, 361, 3240.
[5]
Liu, X.-Y.; Liu, Y.-L.; Chen, L. Adv. Synth. Catal. 2020, 362, 5170
[6]
Fang, Z.; Liu, J.; Liu, Q.; Bi, X. Angew. Chem., nt. Ed. 2014, 53, 7209.
[7]
Hao, L.; Pan, Y.; Wang, T.; Lin, M.; Chen, L.; Zhan, Z.-P. Adv. Synth. Catal. 2010, 352, 3215
[8]
Li, N.; Wang, T.-Y.; Gong, L.-Z.; Zhang, L. Chem.-Eur. J. 2015, 21, 3585.
[9]
Bai, J.-F.; Zhao, L.; Wang, F.; Yan, F.; Kano, T.; Maruoka, K.; Li, Y. Org. Lett. 2020, 22, 5439.
[10]
Wang, X.; Pan, Y.-M.; Huang, X.-C.; Mao, Z.-Y.; Wang, H.-S. Org. Biomol. Chem. 2014, 12, 2028.
[11]
Chong, Q.; Xin, X.; Wang, C.; Wu, F.; Wang, H.; Shi, J.-C.; Wan, B. J. Org. Chem. 2014, 79, 2105.
[12]
Hosseyni, S.; Su, Y.; Shi, X. Org. Lett. 2015, 17, 6010.
[13]
Trofimov, B. A.; Shemyakina, O. A.; Mal'kina, A. G.; Ushakov, I. A.; Kazheva, O. N.; Alexandrov, G. G.; Dyachenko, O. A. Org. Lett. 2010, 12, 3200.
[14]
Minakata, S.; Sasaki, I.; Ide, T. Angew. Chem., nt. Ed. 2010, 49, 1309.
[15]
Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072.
[16]
Yuan, G.-Q.; Zhu, G.-J.; Chang, X.-Y.; Qi, C.-R.; Jiang, H.-F. Tetrahedron 2010, 66, 9981.
[17]
Ca, N. D.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133.
[18]
Song, Q.-W.; Yu, B.; Li, X.-D.; Ma, R.; Diao, Z.-F.; Li, R.-G.; Li, W.; He, L.-N. Green Chem. 2014, 16, 1633.
[19]
Dabral, S.; Bayarmagnai, B.; Hermsen, M.; Schießl, J.; Mormul, V.; Hashmi, A. S. K.; Schaub, T. Org. Lett. 2019, 21, 1422.
[20]
Yan, S.; Zhou, R.; Han, F.; Feng, M.; Miao, C.; Zhang, S.; Ai, S. Catal. Sci. Technol. 2020, 10, 736.
[21]
Yaragorla, S.; Pareek, A.; Dada, R. Adv. Synth. Catal. 2017, 359, 3068.
[22]
Yuan, F.-Q.; Han, F.-S. Adv. Synth. Catal. 2013, 355, 537.
[23]
Yaragorla, S.; Dada, R.; Singh, G.; Pareek, A.; Rana, M.; Sharma, A. K. ChemistrySelect 2016, 1, 6902.
[24]
Pareek, A.; Dada, R.; Rana, M.; Sharma, A. K.; Yaragorla, S. RSC Adv. 2016, 6, 89732.
[25]
Yaragorla, S.; Dada, R.; Pareek, A.; Singh, G. RSC Adv. 2016, 6, 28865.
[26]
Viji, M.; Nagarajan, R. RSC Adv. 2012, 2, 10544.
[27]
Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2006, 71, 4951.
[28]
Bai, L.; Wang, Y.; Wang, S.; Kong, D.; Fu, Y.; Peng, D.; Wen, L.; Chen, X. Chin. J. Org. Chem. 2018, 38, 3242. (in Chinese)
[28]
(白丽丽, 王颖, 王烁今, 孔杜林, 付艳, 彭德乾, 文丽君, 陈训, 有机化学, 2018, 38, 3242.)
[29]
Ponra, S.; Gohain, M.; Donka, R.; van Tonder, J. H.; Bezuidenhoudt, B. C. B. Tetrahedron Lett. 2018, 59, 2909.
[30]
Song, X.; Gao, C.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2018, 83, 8509.
[31]
Wang, S.; Chai, Z.; Wei, Y.; Zhu, X.; Zhou, S.; Wang, S. Org. Lett. 2014, 16, 3592.
[32]
Zeng, H.; Ju, J.; Hua, R. Tetrahedron Lett. 2011, 52, 3926.
[33]
Yaragorla, S.; Pareek, A.; Dada, R. Tetrahedron Lett. 2017, 58, 4642.
[34]
Han, Y.-P.; Li, X.-S.; Zhu, X.-Y.; Sun, Z.; Li, M.; Wang, Y.-Z.; Liang, Y.-M. Adv. Synth. Catal. 2018, 360, 870.
[35]
Liu, Y.; Barry, B.-D.; Yu, H.; Liu, J.; Liao, P.; Bi, X. Org. Lett. 2013, 15, 2608.
[36]
Kitamura, M.; Nishimura, T.; Otsuka, K.; Shimooka, H.; Okauchi, T. Tetrahedron Lett. 2020, 61, 151853.
[37]
Su, J.; Ju, J.; Hua, R. Curr. Org. Synth. 2012, 9, 273.
[38]
Shao, Y.; Zhu, K.; Qin, Z.; Li, E.; Li, Y. J. Org. Chem. 2013, 78, 5731.
[39]
Yin, G.; Zhu, Y.; Wang, N.; Lu, P.; Wang, Y. Tetrahedron 2013, 69, 8353.
[40]
Wang, M.; Tan, C.; He, Q.; Xie, Y.; Yang, C. Org. Biomol. Chem. 2013, 11, 2574.
[41]
Zhang, S.; Shan, C.; Zhang, S.; Yuan, L.; Wang, J.; Tung, C.-H.; Xing, L.-B.; Xu, Z. Org. Biomol. Chem. 2016, 14, 10973.
[42]
Shao, M.; Wu, Y.; Feng, Z.; Gu, X.; Wang, S. Org. Biomol. Chem. 2016, 14, 2515.
[43]
Wu, Y.; Shao, M.; Feng, Z.; Gu, X.; Hong, Y.; Cui, Q.; Ren, L.; Wang, S. Asian J. Org. Chem. 2017, 6, 76.
[44]
Li, X.-S.; Han, Y.-P.; Xu, D.-T.; Li, M.; Wei, W.-X.; Liang, Y.-M. J. Org. Chem. 2020, 85, 2626.
[45]
Wang, L.; Xie, X.; Liu, Y. Angew. Chem., nt. Ed. 2013, 52, 13302.
[46]
Rueping, M.; Dufour, J.; Maji, M. S. Chem. Commun. 2012, 48, 3406.
[47]
Anukumar, A.; Tamizmani, M.; Jeganmohan, M. J. Org. Chem. 2018, 83, 8567.
[48]
Kumar, S.; Nair, A. M.; Volla, C. M. R. Chem. Commun. 2021, 57, 6280.
[49]
Li, Y.; Fang, F.; Zhou, J.; Li, J.; Wang, R.; Liu, H.; Zhou, Y. Adv. Synth. Catal. 2021, 363, 3305.
[50]
Wang, T.-T.; Jin, H.-S.; Cao, M.-M.; Wang, R.-B.; Zhao, L.-M. Org. Lett. 2021, 23, 5952.
[51]
Luo, F.; He, S.; Gou, Q.; Chen, J.; Zhang, M. Tetrahedron Lett. 2021, 64, 152724.
[52]
Qi, C.; Jiang, H.; Huang, L.; Yuan, G.; Ren, Y. Org. Lett. 2011, 13, 5520.
[53]
Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., nt. Ed. 2014, 53, 3715
[54]
Zhang, B.; Wang, T.; Zhang, Z. J. Org. Chem. 2017, 82, 11644
[55]
Wang, J.; Yao, X.; Wang, T.; Han, J.; Zhang, J.; Zhang, X.; Wang, P.; Zhang, Z. Org. Lett. 2015, 17, 5124.
[56]
Shi, T.; Guo, X.; Teng, S.; Hu, W. Chem. Commun. 2015, 51, 15204.
[57]
Le, Z.; Ying, J.; Wu, X.-F. Org. Chem. Front. 2019, 6, 3158.
[58]
Ying, J.; Le, Z.; Wu, X.-F. Org. Chem. Front. 2020, 7, 2757.
[59]
Hsu, Y.-C.; Hsieh, S.-A.; Li, P.-H.; Liu, R.-S. Chem. Commun. 2018, 54, 2114.
[60]
Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A. Org. Lett. 2016, 18, 3511.
[61]
Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Zhang, H.-R.; Li, L.-H.; Jin, D.-P.; Sun, X.-Q.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 940.
[62]
Selvaraj, K.; Debnath, S.; Swamy, K. C. K. Org. Lett. 2019, 21, 5447.
[63]
Yin, G.; Zhu, Y.; Lu, P.; Wang, Y. J. Org. Chem. 2011, 76, 8922.
[64]
Xu, J.; Zhao, J.; Jia, Z.; Zhang, J. Synth. Commun. 2011, 41, 858.
[65]
Liu, H.; Hua, R. Tetrahedron 2016, 72, 1200.
[66]
Hussain, M. K.; Ansari, M. I.; Kant, R.; Hajela, K. Org. Lett. 2014, 16, 560.
[67]
Li, X.-S.; Xu, D.-T.; Niu, Z.-J.; Li, M.; Shi, W.-Y.; Wang, C.-T.; Wei, W.-X.; Liang, Y.-M. Org. Lett. 2021, 23, 832.
[68]
Zhang, L.; Zhao, J.; Jiang, Y.; Zhang, X.; Fan, X. Org. Chem. Front. 2021, 8, 3734.
[69]
Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550.
[70]
Morita, N.; Miyamoto, M.; Yoda, A.; Yamamoto, M.; Ban, S.; Hashimoto, Y.; Tamura, O. Tetrahedron Lett. 2016, 57, 4460.
[71]
Egi, M.; Azechi, K.; Saneto, M.; Shimizu, K.; Akai, S. J. Org. Chem. 2010, 75, 2123
[72]
Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Molinaro, C.; Verdiglione, R. J. Org. Chem. 2014, 79, 401
[73]
Tharra, P.; Baire, B. J. Org. Chem. 2015, 80, 8314
[74]
Egi, M.; Ota, Y.; Nishimura, Y.; Shimizu, K.; Azechi, K.; Akai, S. Org. Lett. 2013, 15, 4150
[75]
Qiu, Y.-F.; Ye, Y.-Y.; Song, X.-R.; Zhu, X.-Y.; Yang, F.; Song, B.; Wang, J.; Hua, H.-L.; He, Y.-T.; Han, Y.-P.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2015, 21, 3480.
[76]
Li, R.; Chen, X.; Song, X.-R.; Ding, H.; Wang, P.; Xiao, Q.; Liang, Y.-M. Adv. Synth. Catal. 2017, 359, 3962.
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