Recent Advances in Cyclization Reactions using N-Vinylamides

  • Chang-Qing Shao ,
  • Kai-Xian Lin ,
  • Yi Xiong ,
  • Xiao-Yu He ,
  • You-Quan Zou
Expand
  • aSchool of Pharmaceutical Sciences, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (MOE), Wuhan University, Hubei Wuhan 430071
These authors contributed equally to this work.

Received date: 2026-04-20

  Revised date: 2026-05-13

  Online published: 2026-07-06

Supported by

Fundamental Research Funds for the Central Universities (No.2042025kf0067), the start-up funding from Wuhan University (No.691000002), and the Wuhan Institute of Photochemistry and Technology Grant (No.GHY2024PY002).

Abstract

N-Vinylamides are an important class of synthetic building blocks, which are widely used in organic synthesis. Their unique structure, strong reactivity, and diverse reaction pathways make them ideal substrates for constructing cyclic frameworks. This review summarizes the recent progresses on cyclization reactions involving N-vinylamides to construct aminocyclopropanes, oxazolines, oxazoles, pyridines, and other cyclic compounds. The reaction mechanisms, substrate scope, stereoselectivity control, and the application of the products are also discussed.

Cite this article

Chang-Qing Shao , Kai-Xian Lin , Yi Xiong , Xiao-Yu He , You-Quan Zou . Recent Advances in Cyclization Reactions using N-Vinylamides[J]. Chinese Journal of Organic Chemistry, 0 : 4012 . DOI: 10.6023/cjoc202604012

References

[1] Bai X.-Y.; Zhang W.-W.; Li Q.; Li, B.-J. J. Am. Chem. Soc.2018, 140, 506-514.
[2] Yang Z.-F.; Xu C.; Zheng X.; Zhang X.-G. Chem. Commun.2020, 56, 2642-2645.
[3] Chang X.-H.; Wang Z.-L.; Zhao M.; Yang C.; Li J.-J.; Ma W.-W.; Xu Y.-H. Org. Lett.2020, 22, 1326-1330.
[4] Damien B.; Thomas V.; Géraldine M. Acc. Chem. Res.2022, 55, 3265-3283.
[5] Cao P.; Xiong W.; Yang T. Org. Lett.2025, 27, 1475-1480.
[6] Le Fouler V.; Duret G.; Bisseret P.; Blanchard N. Tetrahedron Lett.2018, 59, 3349-3352.
[7] Yang Z.-F.; Xu C.; Zheng X.; Zhang X. Chem. Commun.2020, 56, 2642-2645.
[8] Undeela S.; Ravikumar G.; Nanubolu J. B.; Singarapu K. K.; Menon, R. S. Chem. Commun.2016, 52, 4824-4827.
[9] Joanna V.-G.; Andrew J.-C.; Stuart R.-C.; Collette S.-G.; Franco G.; Stephen T. Tetrahedron Letters2016, 57, 3109-3112.
[10] Yu H.; Jiao M.-D.; Fang X.-W.; Xuan P.-F. RSC Adv.2018, 8, 23919-23923.
[11] Li W.-Z.; Shi R.; Chen S.; Zhang X.-S.; Peng W.; Chen S.; Li J.-Z.; Xu X.-M.; Zhu Y.-P.; Wang, X.-Y. J. Org. Chem.2022, 87, 3014-3024.
[12] Zhao C.; Yang S.-H.; Khadka D.B.; Jin Y.; Lee K.-T.; Cho W.-J.Bioorg. Med. Chem. Lett. 2015, 23, 985-995.
[13] Ramurthy S.; Pfister K. B.; Boyce R. S.; Brown S. P.; Costales A. Q.; Desai M. C.; Fang E.; Levine B. H.; Ng S. C.; Nuss J. M.; et al.Bioorg. Med. Chem. Lett. 2020, 30, 126930-126934.
[14] Tarasiuk J.;Kostrzewa-Nowak, D.; Zwierello, W.Molecules 2022, 27, 5138-5160.
[15] Hartwich A.; Zdzienicka N.; Schols D.; Andrei G.; Snoeck R.; Glowacka I. E.Nucleosides Nucleotides Nucleic Acids 2020, 39, 542-591.
[16] Liu J.‐R.; Jiang E.‐Y.; Sukhbaatar O.; Zhang W.‐H.; Zhang M.‐Z.; Yang G.‐F.; Gu Y.‐C.; Med Res Rev.2025, 45, 97-143.
[17] Zhang Z.; Cheng X.; Huang Y.; Wang D.; Lv X.; Chang X.J. Agric. Food Chem. 2025, 73, 3887-3896.
[18] Patel D.; Patel K.; Patel S.; Patel B.; Patel A. ChemistrySelect2024, 9, e202403179.
[19] Guerrero-Pepinosa N. Y.; Cardona-Trujillo M. C.; Garzón-Castaño S. C.;Veloza L. A.; Sepúlveda-Arias, J. C. Biomed. Pharmacother2021, 138, 111495-111509.
[20] Talele, T. T. J. Med. Chem.2016, 59, 8712-8756.
[21] Taylor R. D.; MacCoss M.; Lawson, A. D. G. J. Med. Chem.2014, 57, 5845-5859.
[22] Gagnon A.; Duplessis M.; Fader, L. Org. Prep. Proced. Int.2010, 42, 1-69.
[23] Maekawa, K,; Sasaki T.; Kubo K.; Igarashia T.; Sakurai T.2004, 45, 3663-3667.
[24] Song Z.; Lu T.; Hsung R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y.Angew. Chem. Int. Ed. 2007, 46, 4069-4072.
[25] Lu T.; Song Z.; Hsung R. P.Org Lett. 2008, 10, 541-544.
[26] Chanthamath S.; Nguyen D. T.; Shibatomi K.; Iwasa S. Org. Lett.2013, 15, 772-775.
[27] Xie M.-S.; Zhou P.; Niu H.-Y.; Qu G.-R.; Guo H.-M. Org. Lett.2016, 18, 4344-4347.
[28] Wang H.-X.; Guan F.-J.; Xie M.-S.; Qu G.-R.; Guo, H.-M. Adv. Synth. Catal.2018, 360, 2233-2236.
[29] Chen M.; Zhao M.-N.; Zhang Y.-D.; Ren, Z-H; Guan Z.-H.Sci. China Chem. 2018, 61, 695-701.
[30] Chu Z.; Tang Z.; Zhang K.; Wang L.; Li W.; Wu, H.-H; Zhang, J. Organometallics.2019, 38, 4036-4042.
[31] Zhang J.; Ma Z.; Xu W.; Wang Z.; Chung L.; Xu M.-H. ACS Catal.2024, 14, 9385-9396.
[32] Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Hojati, S. F.Catal. Commun. 2008, 9, 1153-1161.
[33] Jeon H.; Kim D.; Lee J. H.; Song J.; Lee W. S.; Kang D. W.; Kang S.; Lee S. B.; Choi S.; Hong, K. B. Adv. Synth. Catal.2018, 360, 779-783.
[34] Kim H. Y.; Oh K. Org. Lett.2011, 13, 1306-1309.
[35] Jiang Y.-L.; Zhao X.-H.; Chen X.-Y.; Deng Z.-G.; Song D.-G.; Ling F.; Zhong, W.-H. J. Org. Chem.2026, 91, 2983-2990.
[36] Maekawa K.; Hishikawa N.; Kubo K.; Igarashi T.; Sakurai T. Tetrahedron2007, 63, 11267-11281.
[37] Sasaki Y.; Maekawa K.; Watanabe H.; Matsumoto T.; Kubo K.; Igarashi T.; Sakurai T. Tetrahedron Lett.2007, 48 4765-4770.
[38] Battilocchio C.; Bosica F.; Rowe S. M.; Abreu B. L.; Godineau E.; Lehmann M.; Ley, S. V. Org. Process Res. Dev.2017, 21, 1588-1594.
[39] Luo N.; Zhan Z.; Ban Z.; Lu G.; He J.; Hu F.; Huang G.Adv. Synth. Catal. 2020, 362, 3126-3130.
[40] Liu R.-H.; Shan Q.-C.; Gao Y.; Loh T.-P.; Hu, X.-H. Chin. Chem. Lett.2021, 32, 1411-1414.
[41] Sun R.; Yang X.; Ge Y.; Song J.; Zheng X.; Yuan M.; Li R.; Chen H.; Fu H.ACS Catal. 2021, 11, 11762-11773.
[42] Yuan Y.; Zhang F.; Liu X.-C.; Bai C.-Y.; Tao Y.-Y.; Bao X.-Z.; Ji D.-S.; Huo C.-D.Green Chem., 2025, 27, 96-101.
[43] Yuan Y.; Zhang F.; Liu X.-C.; Bai C.-Y.; Jiang H.-F.; Bao X.-Z.; Ji D.-S.; Huo C.-D. Org. Lett.2025, 27, 1841-1846.
[44] Yuan H.-X.; Zhou Y.; Xie X.-D.; Bao M.; Chen K.-W.; Hong K.-M.; Yu Z.-X.; Xu X.-F. Adv. Sci.2025, 12, 2409334-2409342.
[45] Zhou W.; Lu S.-H.; Zhao X.-X.; Wang H.-Y.; Ding C.-H.; Gao M.-C.; Xu B. Org. Lett.2026, 28, 5447-5452.
[46] Shin C. G.; Abe C.; Yonezawa Y. Chem. Lett.2004, 33, 664-665.
[47] Yonezawa Y.; Tani N.; Shin, C.-G. Bull. Chem. Soc. Jpn.2005, 78, 1492-1499
[48] Zheng Y.-H.; Li X.-M.; Ren C.-F.; Daisy Z.-N.; Du Y.-F.; Zhao, K. J. Org. Chem.2012, 77, 10353-10361.
[49] Hempel C.; Nachtsheim B. J.Synlett 2013, 24, 2119-2123.
[50] Kamiya M.; Sonoda M.; Tanimori S. Tetrahedron2017, 73, 1247-1254.
[51] Xu K.; Yang R.-Q.; Yang S.; Jiang C.; Ding Z.-H. Org. Biomol. Chem.2019, 17, 8977-8982.
[52] Chen K.; Wan J.-P.; Zhou L.-Y.; Liu, Y.-Y. J. Mol. Struct.2024, 1308, 138142-138151.
[53] Misra N. C.; Ila, H. J. Org. Chem.2010, 75, 5195-5202.
[54] Tilman L.; Markus G.; Daniel T.; Boris B.; Luise S.; Reinhold Z.; Jürgen P. R.; Dieter L.; Christoph A. S.; Reissig, H. U. Chem. Eur. J.2011, 17, 7480-7491.
[55] Panda N.; Mothkuri, R. New J. Chem.2014, 38, 5727-5736.
[56] Chen Y.-L.; Han W.; Ren Y.-Y.; Ma M.; Ge, D.; Shen, Z.-L.; Guo, K.; Chu, X.-Q.Adv. Sci. 2025, 12, 2404738-2404747.
[57] Yu M.-Z.; Yin G.-G.; Hao Y.-D.; Yan X.-H.; Li F.-Y. Tetrahedron Lett.2026, 175, 155910-155915.
[58] Wendlandt A. E.; Stahl, S. S. Org. Biomol. Chem.2012, 10, 3866-3871.
[59] Cheung C. W.; Buchwald, S. L. J. Org. Chem.2012, 77, 7526-7537.
[60] Yamamoto C.; Takamatsu K.; Hirano K.; Miura, M. J. Org. Chem.2017, 82, 9112-9118.
[61] Ma J.; Zou Q.-J.; Wang C.-H.; Yin G.-W.; Li, F.-Y. J. Org. Chem.2022, 87, 15670-15678.
[62] Zhang W.; Yu W.-L.; Yan Q.-Q.; Liu Z.-X.; Zhang, Y.-H. Org. Chem. Front.2017, 4, 2428-2432.
[63] Sun R.; Yang X.; Ge Y.-C.; Zheng X.-L.; Yuan M.-L.; Li R.-X.; Fu H.-Y.; Chen H.Org. Chem. Front. 2022, 9, 1975-1982.
[64] Ma J.; Wang H.-L.; Meng Q.-Y.; Wang H.-Y.; Li F.-Y.; Li Z. Tetrahedron Lett.2024, 153, 155373-155378.
[65] Wang D.-N.; Lin Q.; Wang, X. Zhang K.-Y.; Duan X.-H.; Liu, L. Asian J. Org. Chem.2023, 12, e202300019.
[66] Farooq S.; Munawar M.; Ngaini Z.Curr. Org. Chem. 2018, 22, 2671-2680.
[67] Fu Y.; Wang P.; Guo X.; Wu P.; Meng X.; Chen B.J. Org. Chem. 2016, 81, 11671-11677.
[68] Zhang X.-Y.; Chen J.; Ma, Y.-M. Chin. J. Org. Chem.2024, 44, 3409-3416.
[69] Singh P.; Sharma A. K.; Singh, K. N. Org. Lett.2026, 28, 5568-5573.
[70] Yamamoto S.; Okamoto K.; Murakoso M.; Kuninobu,Y.; Takai K. Org. Lett.2012, 12, 3182-3185.
[71] Wu J.; Xu W.; Yu Z.-X.; Wang, J. J. Am. Chem. Soc.2015, 137, 9489-9496.
[72] Xu X.-M.; Wang J.; Chen X.; Chen J.; Zhao Z.; Yao Y.; Shao L.; Liu Q.J. Org. Chem. 2025, 90, 3779-3788.
[73] Gao Y.; Peng J.-Y.; Zhang,Y.-N.; Zhao X.-L.; Zhao Y.-L. Org. Biomol. Chem.2025, 23, 4441-4445.
[74] Smolobochkin A.; Gazizov A.; Appazov N.; Sinyashin O.; Burilov, A. Int. J. Mol. Sci.2024, 25, 11158-11184.
[75] Zeng W.; Han C.; Mohammed S.; Li S.; Song Y.; Sun F.; Du, Y. RSC Med. Chem.2024, 15, 788-808.
[76] Franco P.; De Marco I. Polymers.2020, 12, 1114-1142.
[77] Wu J.-W.; He J.; Wang J.-J.; Li L.-X.; Xu C.-Y.; Zhou J.; Li Z.-R.; Xu, H.-J. Chin. J. Org. Chem.2024, 44, 972-980.
[78] Wei N.-N.; Guo W.-Z.; Lu X.; Ren Z.-Q.; Ma H.-J.; Zhang Y.-Q.; Wang J.-J.; Han, B. Chin. J. Org. Chem.2026, 46, 1027-1038.
[79] Yang L.; Wang D.-X.; Huang Z.-T.; Wang, M.-X. J. Am. Chem. Soc.2009, 131, 10390-10391.
[80] Rakshit S.; Patureau F. W.; Glorius, F. J. Am. Chem. Soc.2010, 132, 9585-9587.
[81] Wang L.; Ackermann L. Org. Lett.2013, 15, 176-179.
[82] Li B.; Wang N.; Liang Y.; Xu S.; Wang B. Org. Lett.2013, 15, 136-139.
[83] Yang Z.-X.; Ding L.-C.; Yang G.-H.; Wang D.; Shi L.; Li Y.; Liang, D. J. Org. Chem.2024, 89, 10660-10677.
[84] Tong S.; Wang D.-X.; Zhao, L; Zhu J.; Wang, M.-X. Angew. Chem. Int. Ed.2012, 51, 4417-4420.
[85] Chen M.; Ren Z.-H.; Wang Y.-Y.; Guan, Z.-H.Angew. Chem. Int. Ed. 2013, 52, 14196-14199.
[86] Liu K.; Zou M.; Lei A.J. Org. Chem. 2016, 81, 7088-7092.
[87] Song P.; Yu P.; Lin J.-S.; Li Y.; Yang N.-Y.; Liu X.-Y. Org. Lett.2017, 19, 1330-1333.
[88] Zhang Z.; Zhu C.-J.; Miao M.; Han J.-L.; Ju T.; Song L.; Ye J.-H.; Li J.; Yu D.-G.Chin. J. Chem. 2018, 36, 430-436.
[89] Wang S.; Li X.; Jin S.; Liu K.; Dong C.; Su J.; Song, Q. Org. Chem. Front.2022, 9, 1282-1287.
[90] Zhang X.; Xu X.-M.; Zhao L.; You J.; Zhu J.; Wang M.-X. Tetrahedron Letters2015, 56, 3898-3901.
[91] Ding R.; Fu J.-M.; Tian H.-Y.; Chen N.-S.; Liu L.; Guo Y.; Wang, P.-L. New J. Chem.2021, 45, 11030-11034.
[92] Ding R.; Deng Y.-H.; Luo S.; Tang X.-F.; Liu L.; Wang, P.-L. Org. Chem. Front.2022, 9, 2228-2233.
[93] Ding R.; Zhang B.; Yang L.; Ma T.; Gang D.; Mao Y.-Y.; Gao H.J. Org. Chem. 2024, 89, 1515-1523.
[94] Sun R.; Yang X.; Chen X.; Zhang C.; Zhao X.; Wan X.; Zheng X.; Yuan M.; Fu H.; Li R.; Chen H. Org. Lett.2018, 20, 6755-6759.
[95] Kramer P.; Grimmer J.; Bolte M.; Manolikakes, G. Angew. Chem. Int. Ed.2019, 58, 13056-13059.
[96] Dana S.; Sureshbabu P.; Giri C. K.; Baidya M.Eur. J. Org. Chem. 2021, 1385-1389.
[97] Ma J.; Zou Q.; Yin G.; Li F. Tetrahedron Letters2023, 126, 154646-154649.
[98] Zhou Z.; Ye L.; Yang L.; Li X.; Zhao Z.; Li, X. Org. Chem. Front.2023, 10, 6219-6224.
[99] Qiao X.-X.; Zhao S.-N.; Li Q.; Ma T.; Li G.; He Y.; Zhao X.-J. Org. Lett.2024, 26, 1154-1159.
[100] Xu X.-M.; Wang J.; Chen X.; Zhao Z.; Liu Q.; Tian M.; Sun K.Org. Lett. 2025, 27, 802-807.
Outlines

/