Radical-Mediated Tandem Cyclization to Construct Seven-Membered Nitrogen/Oxygen Heterocycles

doi:10.6023/cjoc202209032

Abstract

Owing to the special chemical structure of the seven-membered heterocyclic skeleton and the unique chemical properties of the heteroatoms contained, it is widely used in natural products and drug molecules. However, the development of synthetic methodology for these structures is challenging due to the unique thermodynamic and kinetic characteristics of nitrogen/oxygen-containing seven-membered heterocyclic frameworks, as well as their own unique cross-ring forces. Therefore, it is of great significance to develop simple and efficient methods for the construction of seven-membered heterocyclic compounds. Compared with traditional synthetic methods, radical reactions can avoid the limitations of poor atom economy and harsh reaction conditions. In this review, the recent synthetic strategies for the construction of seven-membered nitrogen/oxygen-containing heterocyclic compounds using radical tandem cyclization reactions are summarized.

Key words: free radical, cyclization, seven-membered nitrogen heterocycles, seven-membered oxygen heterocycles

Cite this article

Xiaowei Zhao, Ziqin Xia, Man Zhang, Nengneng Zhou. Radical-Mediated Tandem Cyclization to Construct Seven-Membered Nitrogen/Oxygen Heterocycles[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3995-4023.

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Fig. & Tab. 47

Figure 1. Drugs containing seven-membered heterocycles

Figure 2. Synthesis of seven-membered nitrogen heterocycles from oxime ethers

Figure 3. Intramolecular radical cyclization to synthesize seven- membered nitrogen heterocycles

Figure 4. Synthesis of seven-membered nitrogen-containing heterocycles promoted by lauroyl peroxide

Figure 5. Synthesis of seven-membered aza-bicyclic α-lactams by Baylis-Hillman reaction

Figure 6. [2+2] cycloaddition to synthesize tricyclic α-lactams

Figure 7. Synthesis of seven-membered cyclic alkoxyamines by ring expansion

Figure 8. Synthesis of seven-membered nitrogen heterocycles by Stork-catalyzed tin hydride method

Figure 9. Bu3SnH-induced synthesis of seven-membered nitrogen heterocycles

Figure 10. Organophosphorus radical-mediated cyclisations to afford seven-membered lactams

Figure 11. Synthesis of bicyclic α-lactam and tricyclic α-lactam

Figure 12. Visible light-induced synthesis of seven-membered nitrogen heterocycles

Figure 13. Lauroyl peroxide on pyrimidine and aza seven- membered ring

Figure 14. Synthesis of dibenzoazepines from 2-(2-iodophenyl)- N-phenylacetamide

Figure 15. Copper-catalyzed synthesis of sulfonated benzoseven-membered nitrogen heterocycle

Figure 16. Synthesis of seven-membered nitrogen heterocycles via barton ester intermediates

Figure 17. Iron or copper catalyzed the synthesis of trifluoromethyl-containing tetracyclic benzazepines

Figure 18. Silver-catalyzed the synthesis of phosphate indoloazepine derivatives

Figure 19. Copper-catalyzed synthesis of difluoromethylated indoloazepines

Figure 20. Silver-catalyzed synthesis of 2H-benzo[b]azepin-2-ones

Figure 21. Visible light-induced synthesis of benzazepines

Figure 22. Electrochemical synthesis of difluoromethyl-containing dibenzoazepines

Figure 23. Visible light-induced synthesis of fluorinated dibenzo[b,e]azepines

Figure 24. Visible-light-induced synthesis of seven-membered polycyclic lactams and lactones

Figure 25. Copper-catalyzed synthesis of seven-membered nitrogen heterocycles

Figure 26. Cobalt-catalyzed synthesis of cyclic guanidines

Figure 27. Visible-light photoredox catalytic synthesis of sulfonated dibenzoazepines

Figure 28. Copper-catalyzed synthesize of CF3-containing dioxodibenzothiazepines

Figure 29. Photoredox-catalyzed acquisition of difluoroalkylated dibenzoseven-membered azacyclics

Figure 30. AgSCF3-catalyzed synthesis of SCF3-substituted dibenzazepines or dioxydibenzothiazepines

Figure 31. Visible light-induced synthesis of SCN-containing dibenzodiazepine or dioxodibenzothiazepine

Figure 32. Visible light-induced synthesis of difluoroamide sulfonyl dioxodibenzothiazines

Figure 33. Cu-catalyzed synthesize of trifluoromethylthiolated dioxodibenzothiazepines

Figure 34. Copper-catalyzed synthesis of benzo[f][1,2]thiazepine 1,1-dioxide

Figure 35. 7-endo Cyclization triggered by NO2 radicals

Figure 36. Light-induced 7-endo-trig cyclization of N-centered radicals to synthesize seven-membered azacyclics

Figure 37. Synthesis of 2,7-disubstituted epoxyhexane-3-ones from selenides

Figure 38. Synthesis of oxacycles by tandem radical addition- cyclization reactions

Figure 39. Manganese catalyzed synthesis of 9-dibenzo[b,f]oxepane carboxylates

Figure 40. Thiophenol-induced 7-endo cyclization of ortho-vinyl-2-propynyl ethers to synthesize oxepane derivatives

Figure 41. Copper-catalyzed synthesis of sulfinated seven-membered cyclic ethers

Figure 42. Visible light photoredox synthesis of CF2-containing benzoxepane derivatives

Figure 43. Visible light-induced synthesis of sulfonated phenoxyzepines

Figure 44. tert-Butyl hydroperoxide induced synthesis of sulfonated benzoxazepines

Figure 45. Photoredox or metal-catalyzed synthesis of cyanoalkylsulfonylated benzozepines

Figure 46. Synthesis of sulfonated benzo[b]oxeterpenicone derivatives by radical cyclization/sulfonation reaction

Figure 47. Visible light-induced synthesis of bis-difluoroalkylated benoxepines

References 54

[1]	Shimamura, T.; Shiroishi, M.; Weyand, S.; Tsujimoto, H.; Winter, G.; Katritch, V.; Abagyan, R.; Cherezov, V.; Liu, W.; Han, G. W.; Kobayashi, T.; Stevens, R. C.; Iwata, S. Nature 2011, 475, 65. doi: 10.1038/nature10236
[2]	Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511. pmid: 2995669
[3]	Berecz, G.; Dancsó, A.; Németh, D. R.; Kiss, L.; Simig, G.; Volk, B. Synthesis 2022, 54, 3874. doi: 10.1055/s-0040-1719885
[4]	Kumari, P.; Liu, W.; Wang, C. J.; Dai, J.; Wang, M. X.; Yang, Q. Q.; Deng, Y. H.; Shao, Z. Chin. J. Chem. 2020, 38, 151. doi: 10.1002/cjoc.201900430
[5]	Li, X.-H.; Zhang, Z.-L.; Fan, H.-F.; Miao, Y.-L.; Tian, H.-L.; Gu, Y.-C.; Gui, J.-H. J. Am. Chem. Soc. 2021, 143, 4886. doi: 10.1021/jacs.0c13426
[6]	Battiste, M. A.; Pelphrey, P. M.; Wright, D. L. Chem.-Eur. J. 2006, 12, 3438. pmid: 16402402
[7]	Yu, X.-C.; Zhang, C.-C.; Wang, L.-T.; Li, J.-Z.; Li, T.; Wei, W.-T. Org. Chem. Front. 2022, 9, 4757. doi: 10.1039/D2QO00774F
[8]	Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205. doi: 10.1016/S0040-4039(00)76797-9
[9]	Naito, T.; Nakagawa, K.; Nakamura, T.; Kasei, A.; Ninomiya, I.; Kiguchi, T. J. Org. Chem. 1999, 64, 2003. doi: 10.1021/jo9822176
[10]	Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397. doi: 10.1021/jo980208r
[11]	Kaoudi, T.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem., Int. Ed. 2000, 39, 731. doi: 10.1002/(SICI)1521-3773(20000218)39:4【-逻辑与-】#x00026;lt;731::AID-ANIE731【-逻辑与-】#x00026;gt;3.0.CO;2-U
[12]	Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612. pmid: 11262104
[13]	Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. pmid: 14535712
[14]	Schulte, T.; Studer, A. Macromolecules 2003, 36, 3078. doi: 10.1021/ma025806t
[15]	Andrukiewicz, R.; Loska, R.; Prisyahnyuk, V.; Staliński, K. J. Org. Chem. 2003, 68, 1552. pmid: 12585901
[16]	Taniguchi, T.; Ishita, A.; Uchiyama, M.; Tamura, O.; Muraoka, O.; Tanabe, G.; Ishibashi, H. J. Org. Chem. 2005, 70, 1922. pmid: 15730324
[17]	Lang, S.; Corr, M.; Muir, N.; Khan, T. A.; Schönebeck, F.; Murphy, J. A.; Payne, A. H.; Williams, A. C. Tetrahedron Lett. 2005, 46, 4027. doi: 10.1016/j.tetlet.2005.04.032
[18]	Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. J. Org. Chem. 2007, 72, 1604. pmid: 17286433
[19]	O’Connell, J. M.; Moriarty, E.; Aldabbagh, F. Synthesis 2012, 44, 3371. doi: 10.1055/s-0032-1316775
[20]	Liu, Z.-B.; Qin, L.; Zard, S. Z. Org. Lett. 2012, 14, 5976. doi: 10.1021/ol3028829
[21]	Bhakuni, B. S.; Kumar, A.; Balkrishna, S. J.; Sheikh, J. A.; Konar, S.; Kumar, S. Org. Lett. 2012, 14, 2838. doi: 10.1021/ol301077y pmid: 22621204
[22]	Wang, H.-P.; Wang, B.-B.; Sun, S.; Cheng, J. Org. Chem. Front. 2013, 5, 2547. doi: 10.1039/C8QO00615F
[23]	Coyle, R.; Fahey, K.; Aldabbagh, F. Org. Biomol. Chem. 2013, 11, 1672. doi: 10.1039/c3ob27313j
[24]	Yu, L.-Z.; Xu, Q.; Tang, X.-Y.; Shi, M. ACS Catal. 2015, 6, 526. doi: 10.1021/acscatal.5b02400
[25]	Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Wu, X.-X.; Xu, P.-F.; Liang, Y.-M. Org. Lett. 2016, 18, 216. doi: 10.1021/acs.orglett.5b03329
[26]	Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Hu, J.-Y.; Yang, Y.-C.; Liang, Y.-M. Chem. Commun. 2016, 52, 10396. doi: 10.1039/C6CC05745D
[27]	Li, Y.; Hu, M.; Li, J.-H. ACS Catal. 2017, 7, 6757. doi: 10.1021/acscatal.7b02061
[28]	Zhao, Y.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2017, 20, 224. doi: 10.1021/acs.orglett.7b03588
[29]	Xiong, P.; Xu, H.-H.; Song, J.-S.; Xu, H.-C. J. Am. Chem. Soc. 2018, 140, 2460. doi: 10.1021/jacs.8b00391 pmid: 29406700
[30]	Qi, X.-K.; Zhang, H.; Pan, Z.-T.; Liang, R.-B.; Zhu, C.-M.; Li, J.-H.; Tong, Q.-X.; Gao, X.-W.; Wu, L.-Z.; Zhong, J.-J. Chem. Commun. 2019, 55, 10848. doi: 10.1039/C9CC04977K
[31]	Chen, M.-T.; Wei, Y.; Shi, M. Org. Chem. Front. 2019, 7, 374. doi: 10.1039/C9QO01360A
[32]	Zhang, H.-W.; Tian, P.-Y.; Ma, L.-S.; Zhou, Y.-L.; Jiang, C.-Y.; Lin, X.-F.; Xiao, X. Org. Lett. 2020, 22, 997. doi: 10.1021/acs.orglett.9b04542
[33]	Ohuchi, S.; Koyama, H.; Shigehisa, H. ACS Catal. 2021, 11, 900. doi: 10.1021/acscatal.0c05359
[34]	Qu, C.-H.; Song, G.-T.; Ou, J.-H.; Tang, D.-Y.; Xu, Z.-G.; Chen, Z.-Z. Chin. J. Chem. 2021, 39, 2220. doi: 10.1002/cjoc.202100194
[35]	Zhang, Z.-Q.; Xu, Y.-H.; Dai, J.-C.; Li, Y.; Sheng, J.; Wang, X.-S. Org. Lett. 2021, 23, 2194. doi: 10.1021/acs.orglett.1c00344
[36]	Xiao, Q.; Lu, M.-J.; Deng, Y.-L.; Jian, J.-X.; Tong, Q.-X.; Zhong, J.-J. Org. Lett. 2021, 23, 9303. doi: 10.1021/acs.orglett.1c03700
[37]	Ren, Y.-M.; Yan, Q.-Q.; Li, Y.; Gao, Y.-J.; Zhao, J.-C.; Li, L.-J.; Liu, Z.-Q.; Li, Z.-J. J. Org. Chem. 2022, 87, 8773. doi: 10.1021/acs.joc.2c00623
[38]	Chen, S.-L.; Yan, Q.-Q.; Fan, J.; Gao, Y.-J.; Yang, X.-L.; Li, L.-J.; Liu, Z.-Q.; Li, Z.-J. Green Chem. 2022, 24, 4742. doi: 10.1039/D2GC01276F
[39]	Zheng, X.-Y.; Shen, Q.-T.; Yin, C.-L.; Li, L.-H.; Zhong, T.-S.; Yu, C.-M. Adv. Synth. Catal. 2022, 364, 1750. doi: 10.1002/adsc.202200292
[40]	Chen, X.-Y.; Pei, C.-C.; Liu, B.; Li, J.-Y.; Zou, D.-P.; Wu, Y.-J.; Wu, Y.-S. Chem. Commun. 2022, 58, 8674 doi: 10.1039/D2CC02171D
[41]	Zhong, L.-J.; Xiong, Z.-Q.; Ouyang, X.-H.; Li, Y.; Song, R.-J.; Sun, Q.; Lu, X.; Li, J.-H. J. Am. Chem. Soc. 2022, 144, 339. doi: 10.1021/jacs.1c10053
[42]	Sun, K.; Zhang, Y.; Tian, M.; Wang, Z.-C.; Zhao, D.-Y.; Wang, S.-L.; Tang, S.; Zhang, Z. Chem. Commun. 2022, 58, 9658. doi: 10.1039/D2CC02688K
[43]	Boiledieu, W.; Abreu, M. D.; Cuyamendous, C.; Lamaa, D.; Belmont, P.; Brachet, E. Chem. Commun. 2022, 58, 9206. doi: 10.1039/D2CC02780A
[44]	Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252. doi: 10.1021/jo960175k
[45]	Sibi, M. P.; Patil, K.; Rheault, T. R. Eur. J. Org. Chem. 2004, 372.
[46]	Cong, Z.-Q.; Miki, T.; Urakawa, O.; Nishino, H. J. Org. Chem. 2009, 74, 3978. doi: 10.1021/jo9002773
[47]	Majumdar, K. C.; Taher, A. Tetrahedron Lett. 2009, 50, 228. doi: 10.1016/j.tetlet.2008.10.134
[48]	Gao, Y.-L.; Gao, Y.; Tang, X.-D.; Peng, J.-W.; Hu, M.; Wu, W.-Q; Jiang, H.-F. Org. Lett. 2016, 18, 1158. doi: 10.1021/acs.orglett.6b00272
[49]	Xiang, H.-Y.; Zhao, Q.-L.; Xia, P.-J.; Xiao, J.-A.; Ye, Z.-P.; Xie, X.; Sheng, H.; Chen, X.-Q.; Yang, H. Org. Lett. 2018, 20, 1363. doi: 10.1021/acs.orglett.8b00131
[50]	Zhou, N.-N.; Kuang, K.-M.; Wu, M.-X.; Wu, S.-X.; Xia, Z.-Q.; Xu, Q.-K.; Zhang, M. Org. Chem. Front. 2021, 8, 4095. doi: 10.1039/D1QO00611H
[51]	Zhou, N.-N.; Kuang, K.-M.; Wu, M.-X.; Wu, S. -X.; Xu, Q.-K.; Xia, Z.-Q.; Zhang, M. Adv. Synth. Catal. 2021, 363, 3491. doi: 10.1002/adsc.202100466
[52]	Zhou, N.-N.; Wu, S.-X.; Kuang, K.-M.; Xia, Z.-Q.; Xu, Q.-K.; Zhang, M. Org. Chem. Front. 2021, 8, 6032. doi: 10.1039/D1QO01183A
[53]	Yu, Q.-Y.; Zhang, J.-H.; Wu, F.; Liu, X.-Q.; Wang, C.; Zhang, J.-P.; Rong, L.-C. J. Org. Chem. 2022, 87, 7136. doi: 10.1021/acs.joc.2c00361
[54]	Zhou, N.-N.; Xia, Z.-Q.; Kuang, K.-M.; Xu, Q.-K.; Zhao, F.-L.; Wang, L.; Zhang, M. Org. Lett. 2022, 24, 5791. doi: 10.1021/acs.orglett.2c02314

自由基介导的串联环化反应构建七元含氮/氧杂环化合物