Chinese Journal of Organic Chemistry >
Advances in the Synthesis of Azaspiro[4.5]trienones
Received date: 2023-04-04
Revised date: 2023-05-10
Online published: 2023-06-07
Supported by
National Natural Science Foundation of China(21801023); Changsha Municipal Science and Technology Project(kq2004070); Scientific Research Fund of Hunan Provincial Education Department(22B0339); Scientific Research Fund of Hunan Provincial Education Department(22C0160)
As one of the most important structural motifs in natural compounds and active pharmaceutical ingredients, aza- spiro[4.5]trienones derivatives have been widely used in the field of organic synthesis due to their excellent structural properties and biological activities. In recent years, several methods, such as transition metal involvement, visible light promotion, transition metal-free involvement and electrochemical promotion, have been used to efficiently construct various functional groups of azaspiro[4.5]trienones. The recent advances in the synthesis of azaspiro[4.5]trienones are reviewed, and the representative substrates and reaction mechanisms are summarized and discussed.
Jing Tang , Wenkun Luo , Jun Zhou . Advances in the Synthesis of Azaspiro[4.5]trienones[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3006 -3034 . DOI: 10.6023/cjoc202304004
| [1] | (a) Yugandhar D.; Nayak V.-L.; Archana S.; Shekar K.-C.; Srivastava A.-K. Eur. J. Med. Chem. 2015, 101, 348. |
| [1] | (b) Ghoshal A.; Kumar A.; Yugandhar D.; Sona C.; Kuriakose S.; Nagesh K.; Rashid M.; Singh S.-K.; Wahajuddin M.; Yadav P.-N.; Srivastava A.-K. Eur. J. Med. Chem. 2018, 152, 148. |
| [2] | Iskander A. BTL NEDERLAND 2022, 5, 1. |
| [3] | Reddy C.-R.; Prajapti S. K.; Warudikar K.; Ranjan R.; Rao B. B. Org. Biomol. Chem. 2017, 15, 3130. |
| [4] | Song R.; Xie Y. Chin. J. Chem. 2017, 35, 280. |
| [5] | Yang W.-C.; Zhang M.-M.; Feng J.-G. Adv. Synth. Catal. 2020, 362, 4446. |
| [6] | Liang X.-W.; Zheng C.; You S.-L. Chem.-Eur. J. 2016, 22, 11918. |
| [7] | Cheng Y.-Z.; Feng Z.; Zhang X.; You S.-L. Chem. Soc. Rev. 2022, 51, 2145. |
| [8] | Wolfe J.-P. Top Heterocyclic Chemistry, Vol. 32, Ed.: Wolfe, J. P., Springer, Berlin, 2013, p. 1. |
| [9] | Wei W.-T.; Song R.-J.; Ouyang X.-H.; Li Y.; Li H.-B.; Li J.-H. Org. Chem. Front. 2014, 1, 484. |
| [10] | Hua H.-L.; He Y.-T.; Qiu Y.-F.; Li Y.-X.; Song B.; Gao P.; Song X.-R.; Guo D.-H.; Liu X.-Y.; Liang Y.-M. Chem.-Eur. J. 2014, 21, 1468. |
| [11] | Qian P.-C.; Liu Y.; Song R.-J.; Xiang J.-N.; Li J.-H. Synlett 2015, 26, 1213. |
| [12] | Ouyang X.-H.; Song R.-J.; Liu B.; Li J.-H. Chem. Commun. 2016, 52, 2573. |
| [13] | Gao P.; Zhang W.; Zhang Z. Org. Lett. 2016, 18, 5820. |
| [14] | Mo K.; Zhou X.; Wu J.; Zhao Y. Chem. Commun. 2022, 58, 1306. |
| [15] | Reddy C. R.; Kolgave D. H.; Ajaykumar U.; Ramesh R. Org. Biomol. Chem. 2022, 20, 6879. |
| [16] | Wu L.-J.; Tan F.-L.; Li M.; Song R.-J.; Li J.-H. Org. Chem. Front. 2017, 4, 350. |
| [17] | Wang J.; Lu X.-X.; Yang R.-P.; Xiang Z.-H.; Zhang B.-B.; Chao S.; Liu L.; Yan Y.; Shang X. J. Org. Chem. 2022, 87, 13089. |
| [18] | Wang L.-J.; Wang A.-Q.; Xia Y.; Wu X.-X.; Liu X.-Y.; Liang Y.-M. Chem. Commun. 2014, 50, 13998. |
| [19] | Cui H.; Wei W.; Yang D.; Zhang J.; Xu Z.; Wen J.; Wang H. RSC Adv. 2015, 5, 84657. |
| [20] | Jin D.-P.; Gao P.; Chen D.-Q.; Chen S.; Wang J.; Liu X.-Y.; Liang Y.-M. Org. Lett. 2016, 14, 3486. |
| [21] | Vacala T. L.; Carlson P. R.; Arreola-Hester A.; Williams C. G.; Makhoul E. W.; Vadola P. A. J. Org. Chem. 2018, 83, 1493. |
| [22] | Yuan J.-W.; Mou C.-X.; Zhang Y.; Hu W.-Y.; Yang L.-R.; Xiao Y.-M.; Mao P.; Zhang S.-R.; Qu L.-B. Org. Biomol. Chem. 2021, 19, 10348. |
| [23] | Reddy C. R.; Kolgave D. H.; Subbarao M.; Aila M.; Prajapti S. K. Org. Lett. 2022, 22, 5342. |
| [24] | Reddy C. R.; Subbarrao M.; Kolgave D. H.; Ajaykumar U.; Vinaya P. P. ACS Omega 2022, 7, 38045. |
| [25] | Li M.; Song R.-J.; Li J.-H. Chin. J. Chem. 2017, 35, 299. |
| [26] | He Y. C.; Qiu G. Org. Biomol. Chem. 2017, 15, 3485. |
| [27] | Xia Y.; Wang L.-J.; Wang J.; Chen S.; Guo C.-H.; Liang Y.-M. J. Org. Chem. 2017, 82, 12386. |
| [28] | Gao W.-C.; Liu T.; Cheng Y.-F.; Chang H.-H.; Li X.; Zhou R.; Wei W.-L.; Qiao Y. J. Org. Chem. 2017, 82, 13459. |
| [29] | Qiao Z.; Shao C.; Gao Y.; Liang K.; Yin H.; Chen F.-X. Tetrahedron Lett. 2022, 100, 153875. |
| [30] | Bansode A. H.; Shaikh S. R.; Gonnade R. G.; Patil N. T. Chem. Commun. 2017, 53, 9081. |
| [31] | Wei W.; Cui H.; Yang D.; Yue H.; He C.; Zhang Y.; Wang H. Green Chem. 2017, 19, 5608. |
| [32] | Sahoo H.; Mandal A.; Dana S.; Baidya M. Adv. Synth. Catal. 2018, 360, 1099. |
| [33] | Chen Y.; Chen Y.-J.; Guan Z.; He Y.-H. Tetrahedron 2019, 75, 130763. |
| [34] | Liu T.; Li Y.; Jiang L.; Wang J.; Jin K.; Zhang R.; Duan C. Org. Biomol. Chem. 2020, 18, 1933. |
| [35] | Zhang N.; Zuo H.; Xu C.; Pan J.; Sun J.; Guo C. Chin. Chem. Lett. 2020, 31, 337. |
| [36] | Manna S.; Ashwathappa P. K. S.; Prabhu K. R. Chem. Commun. 2020, 56, 13165. |
| [37] | Zeng F.-L.; Chen X.-L.; Sun K.; Zhu H.-L.; Yuan X.-Y.; Liu Y.; Qu L.-B.; Zhao Y.-F.; Yu B. Org. Chem. Front. 2021, 8, 760. |
| [38] | Chen Y.; Lu F.-Y.; Li R.-X.; Guan Z.; He Y.-H. Asian J. Org. Chem. 2021, 10, 668. |
| [39] | Zhu H.-L.; Zeng F.-L.; Chen X.-L.; Sun K.; Li H.-C.; Yuan X.-Y.; Qu L.-B.; Yu B. Org Lett. 2021, 23, 2976. |
| [40] | Zeng F.-L.; Zhu H.-L.; Chen X.-L.; Qu L.-B.; Yu B. Green Chem. 2021, 23, 3677. |
| [41] | Yuan J.-W.; Shen L.; Ma M.-Y.; Feng S.; Yang W.; Yang L.-R.; Xiao Y.-M.; Zhang S.-R.; Qu L.-B. New J. Chem. 2022, 46, 4470. |
| [42] | Zhou T.; Liu R.; Wang X.; Rui M.; Zhao X.; Lu K. Asian. J. Org. Chem. 2022, 11, e202200154. |
| [43] | Yang M.; Hua J.-W.; Wang H.; Ma T.; Liu C.-K.; He W.; Zhu N.; Hu Y.; Fang Z.; Kai G. J. Org. Chem. 2022, 87, 8445. |
| [44] | Manna S.; Prabhu K. R. Org. Lett. 2023, 25, 810. |
| [45] | Liu Y.; Wang Q.-L.; Zhou C.-S.; Xiong B.-Q.; Zhang P.-L.; Yang C.-A.; Tang K.-W. J. Org. Chem. 2018, 83, 2210. |
| [46] | Liu Y.; Wang Q.-L.; Xiong B.-Q.; Zhang P.-L.; Yang C.-A.; Gong Y.-X.; Liao J.; Zhou Q. Synlett 2018, 29, 2396. |
| [47] | Liu Y.; Wang Q.-L.; Chen Z.; Zhou Q.; Xiong B.-Q.; Zhang P.-L.; Tang K.-W. Chem. Commun. 2019, 55, 12212. |
| [48] | Nair A.; Halder I.; Khan S.; Volla C. M. R. Adv. Synth. Catal. 2020, 362, 224. |
| [49] | Chen P.; Xie J.; Chen Z.; Xiong B.-Q.; Liu Y.; Yang C.-A.; Tang K.-W. Adv. Synth. Catal. 2021, 363, 4440. |
| [50] | Tang B.-X.; Zhang Y.-H.; Song R.-J.; Tang D.-J.; Deng G.-B.; Wang Z.-Q.; Xie Y.-X.; Xia Y.-Z.; Li J.-H. J. Org. Chem. 2012, 77, 2837. |
| [51] | Ouyang X.-H.; Song R.-J.; Li Y.; Liu B.; Li J.-H. J. Org. Chem. 2014, 79, 4582. |
| [52] | Yang X.-H.; Ouyang X.-H.; Wei W.-T.; Song R.-J.; Li J.-H. Adv. Synth. Catal. 2015, 357, 1161. |
| [53] | Wen J; Wei W.; Xue S.; Yang D.; Lou Y.; Gao C.; Wang H. J. Org. Chem. 2015, 80, 4966. |
| [54] | Yugandhar D.; Srivastava A. K. ACS Comb. Sci. 2015, 17, 474. |
| [55] | Yugandhar D.; Kuriakose S.; Nanubolu J. B.; Srivastava A. K. Org. Lett. 2016, 18, 1040. |
| [56] | Reddy C. R.; Yarlagadda S.; Ramesh B.; Reddy M. R.; Sridhar B.; Reddy B. V. S. Eur. J. Org. Chem. 2017, 2017, 2332. |
| [57] | Wang C.-S.; Roisnel T.; Dixneuf P. H.; Soulé J.-F. Adv. Synth. Catal. 2019, 361, 445. |
| [58] | Recchi A. M. S.; Rosa P. H. P.; Back D. F.; Zeni G. Org. Biomol. Chem. 2020, 18, 3544. |
| [59] | Sahoo H.; Grandhi G. S.; Ramakrishna I.; Baidya M. Org. Biomol. Chem. 2019, 17, 10163. |
| [60] | Li X.; Zhang B.; Yu Z.; Zhang D.; Shi H.; Xu L.; Du Y. Synthesis 2022, 54, 1375. |
| [61] | (a) Yuan J.-W.; Huang G.-C.; Wang L.-L.; Wang X.-Y.; Yang L.-R.; Zhang S.-R.; Mao P.; Xiao Y.-M.; Qu L.-B. Z. Natur- forsch., B 2022, 77, 75. |
| [61] | (b) Yuan J.-W.; Chen Q.; Wu W.-T.; Zhao J.-J.; Yang L.-R.; Xiao Y.-M.; Mao P.; Qu L.-B. New. J. Chem. 2022, 46, 9451. |
| [62] | Nair A. M.; Shinde A. H.; Kumar S.; Volla C. M. R. Chem. Commun. 2020, 56, 12367. |
| [63] | Li X.; Wang Y.; Ouyang Y.; Yu Z.-Y.; Zhang B.; Zhang J.; Shi H.; Zuilhof H.; Du Y. J. Org. Chem. 2021, 86, 9490. |
| [64] | Li X.; Zhang B.; Zhao B.; Wang X.; Xu L.; Du Y. Adv. Synth. Catal. 2022, 364, 1427. |
| [65] | Chen P.; Fan J.-H.; Yu W.-Q.; Xiong B.-Q.; Liu Y.; Tang K.-W.; Xie J. J. Org. Chem. 2022, 87, 5643. |
| [66] | Wang Q.; Liu H.-F.; Ren S.-Y.; He M.-X.; Pan Y.-M. Synthesis 2023, DOI: 10.1055/a-2019-0399. |
| [67] | Hua J.; Fang Z.; Bian M.; Ma T.; Yang M.; Xu J.; Liu C.; He W.; Zhu N.; Yang Z.; Guo K. ChemSusChem 2020, 13, 2053. |
| [68] | Yu K.; Kong X.; Yang J.; Li G.; Xu B.; Chen Q. J. Org. Chem. 2021, 86, 917. |
| [69] | Chen Z.; Tang W.; Yang S.; Yang L. Green Synth. Catal. 2023, DOI: 10.1016/j.gresc.2022.09.006. |
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