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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 7: 2323 - 2337

DOI: https://doi.org/10.6023/cjoc202212036

REVIEWS

Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy

  • Yuzhuo Chen ,
  • Hongmei Sun ,
  • Liang Wang ,
  • Fangzhi Hu ,
  • Shuaishuai Li
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  • College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
†The authors contributed equally to this work
*E-mail: ;

Received date: 2022-12-29

  Revised date: 2023-02-22

  Online published: 2023-03-24

Supported by

National Natural Science Foundation of China(21978144); National Natural Science Foundation of China(22208184); Support Plan on Science and Technology for Youth Innovation of Universities in Shandong Province(2019KJM002)

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Abstract

The efficient construction of heterocyclic compounds is an important topic in the field of organic synthesis. [m＋n] cyclization reaction can form privilege molecules from the combination of two readily available reaction substrates, which is an important means for construction of cyclic skeletons. The [m＋n] cyclization reaction based on hydride transfer strategy can in situ generate hydride acceptor from two relatively simple substrates, avoiding the prefabrication of reaction substrates, which features high atom and step economy. In this review, the [m＋n] cyclization reactions based on hydride transfer strategy are selected as the research object. Starting from the framework of aza- and oxa-heterocycles constructed by this kind of reaction, this review is classified according to the size of the generated aza- and oxa-heterocycles. The recent progress of [m＋n] cyclization based on hydride transfer strategy since 2018 is summarized, and the development of this field is also prospected.

Key words： heterocyclic compounds; hydride-transfer strategy; [m＋n] cyclization

Cite this article

Yuzhuo Chen , Hongmei Sun , Liang Wang , Fangzhi Hu , Shuaishuai Li . Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2323 -2337 . DOI: 10.6023/cjoc202212036

References

[1]
(a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
[1]
(b) Delost, M. D.; Smith, D. T.; Anderson, B. J.; Njardarson, J. T. J. Med. Chem. 2018, 61, 10996.
[1]
(c) Bhutani, P.; Joshi, G.; Raja, N.; Bachhav, N.; Rajanna, P. K.; Bhutani, H.; Paul, A. T.; Kumar, R. J. Med. Chem. 2021, 64, 2339.
[1]
(d) Wang, L.; Zhang, Z.; Han, H.; Liu, X.; Bu, Z.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 12 (in Chinese).
[1]
(王乐乐, 张子莹, 韩华彬, 刘雄利, 卜站伟, 王琪琳, 有机化学, 2021, 41, 12.)
[1]
(e) Zhang, H.; Shi, F. Chin. J. Org. Chem. 2022, 42, 3351 (in Chinese).
[1]
(张洪浩, 石枫, 有机化学, 2022, 42, 3351.)
[1]
(f) Zhang, Z.; Han, H.; Wang, L.; Bu, Z.; Xie, Y.; Wang, Q. Org. Biomol. Chem. 2021, 19, 3960.
[1]
(g) Zhang, W. H.; Chen, S.; Liu, X. L.; Lin, B.; Liu, X. W.; Zhou, Y. Bioorg. Med. Chem. Lett. 2020, 30, 127410.
[1]
(h) Zhang, M.; Wang, J.-X.; Chang, S.-Q.; Liu, X.-L.; Zuo, X.; Zhou, Y. Chin. Chem. Lett. 2020, 31, 381.
[1]
(i) Wang, L.; Han, H.; Gu, L.; Zhang, W.; Zhao, J.; Wang, Q. Chem. Sci. 2021, 12, 15389.
[2]
(a) Muthukrishnan, I.; Sridharan, V.; Menendez, J. C. Chem. Rev. 2019, 119, 5057.
[2]
(b) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
[2]
(c) Wang, Y.; Zhang, W.-X.; Xi, Z. Chem. Soc. Rev. 2020, 49, 5810.
[3]
For reviews on the formal 4＋1 annulation reactions, see: a Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
[3]
(b) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Rev. 2015, 115, 5301.
[4]
For reviews on the formal 4＋2 annulation reactions, see: a Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779.
[4]
(b) Li, J.-L.; Liu, T.-Y.; Chen, Y.-C. Acc. Chem. Res. 2012, 45, 1491.
[4]
(c) Jiang, X.-X.; Wang, R. Chem. Rev. 2013, 113, 5515.
[5]
(a) For reviews on the formal 4＋3 annulation reactions, see: Harmata, M. Chem. Commun. 2010, 46, 8886.
[5]
(b) Lohse, A. G.; Hsung, R. P. Chem.-Eur. J. 2011, 17, 3812.
[5]
(c) Nguyen, T. V.; Hartmann, J. M.; Enders, D. Synthesis 2013, 845.
[6]
For reviews on hydride transfer reactions, see: (b) Hu, F.; Shen, Y.-B.; Wang, L.; Li, S.-S. Org. Chem. Front. 2022, 9, 5041.
[6]
(b) Shen, Y.-B.; Hu, F.; Li, S.-S. Tetrahedron 2022, 127, 133089.
[6]
(c) Liu, H.; Quan, Y.; Xie, L.; Li, X.; Xie, X. Front. Chem. 2022, 10, 840934.
[6]
(d) An, X.-D.; Xiao, J. Org. Chem. Front. 2021, 8, 1364.
[6]
(e) Kwon, S. J.; Kim, D. Y. Chem. Rec. 2016, 16, 1191.
[6]
(f) Wang, L.; Xiao, J. Top. Curr. Chem. 2016, 374, 17.
[6]
(g) Haibach, M. C.; Seidel, D. Angew. Chem., Int. Ed. 2014, 53, 5010.
[6]
(h) Wang, L.; Xiao, J. Adv. Synth. Catal. 2014, 356, 1137.
[6]
(i) Peng, B.; Maulide, N. Chem.-Eur. J. 2013, 19, 13274.
[6]
(j) Pan, S. C. Beilstein J. Org. Chem. 2012, 8, 1374.
[6]
(k) Shen, Y.-B.; Hu, F.; Li, S.-S. Org. Biomol. Chem. 2023, 21, 700.
[7]
For selected examples on hydride transfer reaction, see: (a) Mori, K.; Kawasaki, T.; Sueoka, S.; Akiyama, T. Org. Lett. 2010, 12, 1732.
[7]
(b) Mori, K.; Sueoka, S.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 2424.
[7]
(c) Yamazaki, S.; Naito, T.; Niina, M.; Kakiuchi, K. J. Org. Chem. 2017, 82, 6748.
[7]
(d) Jeong, H. I.; Youn, T. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2017, 38, 421.
[7]
(e) Briones, J. F.; Basarab, G. S. Chem. Commun. 2016, 52, 8541.
[7]
(f) Yoshida, T.; Mori, K. Chem. Commun. 2017, 53, 4319.
[7]
(g) Yamazaki, S.; Naito, T.; Tatsumi, T.; Kakiuchi, K. Chemistry Select 2018, 3, 4505.
[7]
(h) Yoshida, T.; Mori, K. Chem. Commun. 2018, 54, 12686.
[7]
(i) Yokoo, K.; Mori, K. Chem. Commun. 2018, 54, 6927.
[7]
(j) Ramakumar, K.; Maji, T.; Partridge, J. J.; Tunge, J. A. Org. Lett. 2017, 19, 4014.
[7]
(k) Kataoka, M.; Otawa, Y.; Ido, N.; Mori, K. Org. Lett. 2019, 21, 9334.
[7]
(l) Mori, K.; Isogai, R.; Kamei, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2018, 140, 6203.
[7]
(m) Mori, K.; Umehara, N.; Akiyama, T. Chem. Sci. 2018, 9, 7327.
[7]
(n) Shen, Y.-B.; Li, L.-F.; Xiao, M.-Y.; Yang, J.-M.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84, 13935.
[7]
(o) Yokoo, K.; Mori, K. Org. Lett. 2020, 22, 244
[7]
(p) Paul, A.; Chandak, H. S.; Ma, L.; Seidel, D. Org. Lett. 2020, 22, 976.
[8]
(a) Spadoni, G.; Bedini, A.; Lucarini, S.; Mari, M.; Caignard, D.-H.; Boutin, J. A.; Delagrange, P.; Lucini, V.; Scaglione, F.; Lodola, A.; Zanardi, F.; Pala, D.; Mor, M.; Rivara, S. J. Med. Chem. 2015, 58, 7512.
[8]
(b) Taylor, S. N.; Marrazzo, J.; Batteiger, B. E.; Hook, E. W.; Se?a, A. C.; Long, J.; Wierzbicki, M. R.; Kwak, H.; Johnson, S. M.; Lawrence, K.; Mueller, J. N. Engl. J. Med. 2018, 379, 1835.
[8]
(c) Costa, M.; Dias, T. A.; Brito, A.; Proenca, F. Eur. J. Med. Chem. 2016, 123, 487.
[8]
(d) Pratap, R.; Ram, V. J. Chem. Rev. 2014, 114, 10476.
[8]
(e) Gu, L.-J.; Han, H.-B.; Bu, Z.-W.; Wang, Q.-L. Org. Lett. 2022, 24, 2008.
[8]
(f) Miao, H.-J.; Wang, L.-L.; Han, H.-B.; Zhao, Y.-D.; Wang, Q.-L.; Bu, Z.-W. Chem. Sci. 2020, 11, 1418.
[8]
(g) Bai, X.-G.; Miao, H.-J.; Zhao, Y.; Wang, Q.-L.; Bu, Z.-W. Org. Lett. 2020, 22, 5068.
[9]
Liu, S.; Zhang, W.; Qu, J.; Wang, B. Org. Chem. Front. 2018, 5, 3008.
[10]
Yuan, K.; Dong, F.; Yin, X.; Li, S.-S.; Wang, L.; Xu, L. Org. Chem. Front. 2020, 7, 3868.
[11]
Guo, M.; Dong, F.; Yin, X.; Xu, L.; Wang, L.; Li, S.-S. Org. Chem. Front. 2021, 8, 2224.
[12]
Yang, X.; Liu, J.; Hu, F.; Sun, H.; Wang, L.; Li, S.-S. Chin. J. Org. Chem. 2021, 41, 2788 (in Chinese).
[12]
(杨晓宇, 柳建林, 胡方芝, 孙红梅, 王亮, 李帅帅, 有机化学, 2021, 41, 2788.)
[13]
(a) Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009, 74, 419.
[13]
(b) Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T. Chem. Lett. 2009, 38, 524.
[13]
(c) Du, Y.; Luo, S.; Gong, L. Tetrahedron Lett. 2011, 52, 7064.
[13]
(d) Shen, Y.-B.; Wang, L.-X.; Sun, Y.-M.; Dong, F.-Y.; Yu, L.; Liu, Q.; Xiao, J. J. Org. Chem. 2020, 85, 1915.
[13]
(e) Dong, F.; Song, X.; Yin, X.; Wang, L. ChemistrySelect 2022, 7, e202203936.
[14]
Shi, H.; Xu, L.; Ren, D.; Wang, L.; Guo, W.; Li, S.-S. Org. Biomol. Chem. 2020, 18, 895.
[15]
Chen, C.; Xu, L.; Wang, L.; Li, S.-S. Org. Biomol. Chem. 2018, 16, 7109.
[16]
Liu, S.; Wang, H.; Wang, B. Org. Biomol. Chem. 2020, 18, 8839.
[17]
Yang, X.; Hu, F.; Wang, L.; Xu, L.; Li, S.-S. Org. Biomol. Chem. 2020, 18, 4267.
[18]
Li, S.-S.; Zhu, S.; Chen, C.; Duan, K.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21, 1058.
[19]
Zhu, S.; Chen, C.; Duan, K.; Sun, Y.-M.; Li, S.-S.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84, 8440.
[20]
Wang, P.-F.; Jiang, C.-H.; Wen, X.; Xu, Q.-L.; Sun, H. J. Org. Chem. 2015, 80, 1155.
[21]
Li, S.-S.; Lv, X.; Ren, D.; Shao, C.-L.; Liu, Q.; Xiao, J. Chem. Sci. 2018, 9, 8253.
[22]
Duan, K.; Shi, H.; Wang, L.-X.; Li, S.-S.; Xu, L.; Xiao, J. Org. Chem. Front. 2020, 7, 2511.
[23]
Ge, C.; Wang, L.; Hu, F.; Ding, Z.; Li, X.; Xiao, D.; Wang, J.; Li, S.-S. Org. Chem. Front. 2022, 9, 1696.
[24]
Cao, L.; Hu, F.; Sun, H.; Zhang, X.; Li, S.-S. Org. Chem. Front. 2022, 9, 1668.
[25]
(a) Feuston, B. P.; Culberson, J. C.; Duggan, M. E.; Hartman, G. D.; Leu, C.-T.; Rodan, S. B. J. Med. Chem. 2002, 45, 5640.
[25]
(b) Sum, F.; Dusza, J.; Delos Santos, E.; Grosu, G.; Reich, M.; Du, X.; Albright, J. D.; Chan, P.; Coupet, J.; Ru, X.; Mazandarani, H.; Saunders, T. Bioorg. Med. Chem. Lett. 2003, 13, 2195.
[25]
(c) Kunick, C.; Bleeker, C.; Pru?hs, C.; Totzke, F.; Schachtele, C.; Kubbutat, M. H. G.; Link, A. Bioorg. Med. Chem. Lett. 2006, 16, 2148.
[25]
(d) Palma, A.; Yepes, A. F.; Leal, S. M.; Coronado, C. A.; Escobar, P. Bioorg. Med. Chem. Lett. 2009, 19, 2360.
[25]
(e) Xu, Y.; Zhang, L.; Liu, M.; Zhang, X.; Zhang, X.; Fan, X. Org. Biomol. Chem. 2019, 17, 8706.
[25]
(g) Wang, L.-L.; Han, H.-B.; Cui, Z.-H.; Zhao, J.-W.; Bu, Z.-W.; Wang, Q.-L. Org. Lett. 2020, 22, 873.
[25]
(h) Liu, J.; Xiao, X.; Lai, Y.; Zhang, Z. Org. Chem. Front. 2022, 9, 2256.
[26]
Liu, S.; Zhao, T.; Qu, J.; Wang, B. Adv. Synth. Catal. 2018, 360, 4094.
[27]
Wang, S.; Shen, Y.-B.; Li, L.-F.; Qiu, B.; Yu, L.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21, 8904.
[28]
Bai, G.; Dong, F.; Xu, L.; Liu, Y.; Wang, L.; Li, S.-S. Org. Lett. 2019, 21, 6225.
[29]
Xie, R.; Chen, S.; Wang, Y.; Yin, X.; Li, S.-S.; Xu, L.; Wang, L. Org. Chem. Front. 2022, 9, 5205.
[30]
Yang, X.; Wang, L.; Hu, F.; Xu, L.; Li, S.; Li, S.-S. Org. Lett. 2021, 23, 358.
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