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Synthesis 2023; 55(14): 2219-2227
DOI: 10.1055/a-2052-3331
DOI: 10.1055/a-2052-3331
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry
Aliphatic Acylhydrazides as Effective Alkylating Agents for the Copper-Catalyzed Oxidative Cyclization of N-Arylacrylamides
The project was supported by the National Natural Science Foundation of China (22271269).
Dedicated to Professor Guoqiang Lin on the occasion of his 80th birthday.
Abstract
An unprecedented use of readily accessible aliphatic acylhydrazides as alkylating agents has been demonstrated in the copper-catalyzed tandem alkylation/cyclization of N-arylacrylamides. A range of aliphatic acylhydrazides smoothly participated in the oxidative 5-exo-trig cyclization of N-arylacrylamides with CuCO3 as the catalyst and DTBP as the oxidant, delivering structurally diverse 3,3-dialkyloxindoles in moderate to good yields. This study paves the way for the synthetic applications of aliphatic acylhydrazides as alkyl radical precursors.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2052-3331.
- Supporting Information
Publication History
Received: 10 February 2023
Accepted after revision: 10 March 2023
Accepted Manuscript online:
10 March 2023
Article published online:
13 April 2023
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References
- 1a Yang F.-L, Tian S.-K. Tetrahedron Lett. 2017; 58: 487
- 1b Hosseinian A, Mohammadi R, Ahmadi S, Monfared A, Rahmani Z. RSC Adv. 2018; 8: 33828
- 1c Zhao S, Chen K, Zhang L, Yang W, Huang D. Adv. Synth. Catal. 2020; 362: 3516
- 1d Mulina OM, Ilovaisky AI, Parshin VD, Terent’ev AO. Adv. Synth. Catal. 2020; 362: 4579
- 1e Tu Y, Zhao J. Chem. Rec. 2021; 21: 3442
- 2a Braslau R, Anderson MO, Rivera F, Jimenez A, Haddad T, Axon JR. Tetrahedron 2002; 58: 5513
- 2b Ma H.-Y, Zha Z.-G, Zhang Z.-L, Meng L, Wang Z.-Y. Chin. Chem. Lett. 2013; 24: 780
- 2c Liu G, Jin C, Wu G. Synlett 2014; 25: 2908
- 2d Xie S, Su L, Mo M, Zhou W, Zhou Y, Dong J. J. Org. Chem. 2021; 86: 739
- 2e Hafeez S, Saeed A. RSC Adv. 2021; 11: 38683
- 2f Wang Y.-J, Zhang G.-Y, Shoberu A, Zou J.-P. Tetrahedron Lett. 2021; 80: 153316
- 2g Zhang H, Wang T, Xu K, Zeng C. J. Org. Chem. 2021; 86: 16171
- 2h Tian L, Zhang Q, Ablajan K. Synthesis 2022; 54: 4353
- 2i Alam T, Rakshit A, Dhara HN, Palai A, Patel BK. Org. Lett. 2022; 24: 6619
- 3a Li C, Li P, Yang J, Wang L. Chem. Commun. 2012; 48: 4214
- 3b Zhang Y.-G, Liu X.-L, He Z.-Y, Li X.-M, Kang H.-J, Tian S.-K. Chem. Eur. J. 2014; 20: 2765
- 3c Liu C, Yang F. Chin. J. Chem. 2016; 34: 1213
- 3d Dong J, Liu L, Ji X, Shang Q, Liu L, Su L, Chen B, Kan R, Zhou Y, Yin S.-F, Han L.-B. Org. Lett. 2019; 21: 3198
- 4a Chen J.-R, Yu X.-Y, Xiao W.-J. Synthesis 2015; 47: 604
- 4b Song R.-J, Liu Y, Xie Y.-X, Li J.-H. Synthesis 2015; 47: 1195
- 5a Cui C.-B, Kakeya H, Osada H. J. Antibiot. 1996; 49: 832
- 5b Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R. J. Med. Chem. 2001; 44: 4641
- 5c Yeung BK, Zou B, Rottmann M, Lakshminarayana SB, Ang SH, Leong SY, Tan J, Wong J, Keller-Maerki S, Fischli C, Goh A, Schmitt EK, Krastel P, Francotte E, Kuhen K, Plouffe D, Henson K, Wagner T, Winzeler EA, Petersen F, Brun R, Dartois V, Diagana TT, Keller TH. J. Med. Chem. 2010; 53: 5155
- 5d Vintonyak VV, Warburg K, Kruse H, Grimme S, Hubel K, Rauh D, Waldmann H. Angew. Chem. Int. Ed. 2010; 49: 5902 ; Angew. Chem. 2010, 122, 6038
- 6a Zhou S.-L, Guo L.-N, Wang H, Duan X.-H. Chem. Eur. J. 2013; 19: 12970
- 6b Zhou M.-B, Wang C.-Y, Song R.-J, Liu Y, Wei W.-T, Li J.-H. Chem. Commun. 2013; 49: 10817
- 6c Li Z, Zhang Y, Zhang L, Liu Z.-Q. Org. Lett. 2014; 16: 382
- 6d Tan Z, Jiang Y, Xu K, Zeng C. J. Catal. 2023; 417: 473
- 7a Fan J.-H, Zhou M.-B, Liu Y, Wei W.-T, Ouyang X.-H, Song R.-J, Li J.-H. Synlett 2014; 25: 657
- 7b Dai Q, Yu J, Jiang Y, Guo S, Yang H, Cheng J. Chem. Commun. 2014; 50: 3865
- 7c Xu Z, Yan C, Liu Z.-Q. Org. Lett. 2014; 16: 5670
- 8 Zhao Y, Li Z, Sharma UK, Sharma N, Song G, Van der Eycken EV. Chem. Commun. 2016; 52: 6395
- 9a Biswas P, Paul S, Guin J. Angew. Chem. Int. Ed. 2016; 55: 7756 ; Angew. Chem. 2016, 128, 7887
- 9b Yang L, Lu W, Zhou W, Zhang F. Green Chem. 2016; 18: 2941
- 10a Wu T, Zhang H, Liu G. Tetrahedron 2012; 68: 5229
- 10b Xie J, Xu P, Li H, Xue Q, Jin H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 5672
- 11 Tang Q, Liu X, Liu S, Xie H, Liu W, Zeng J, Cheng P. RSC Adv. 2015; 5: 89009
- 12a Tian Q, He P, Kuang C. Org. Biomol. Chem. 2014; 12: 6349
- 12b Shi L, Wang H, Yang H, Fu H. Synlett 2015; 26: 688
- 12c Qiu J.-K, Hao W.-J, Kong L.-F, Ping W, Tu S.-J, Jiang B. Tetrahedron Lett. 2016; 57: 2414
- 12d Yu J.-T, Hu W, Peng H, Cheng J. Tetrahedron Lett. 2016; 57: 4109
- 13a Rong G, Mao J, Yan H, Zheng Y, Zhang G. J. Org. Chem. 2015; 80: 4697
- 13b He Z.-Y, Huang C.-F, Tian S.-K. Org. Lett. 2017; 19: 4850
- 13c He Z.-Y, Guo J.-Y, Tian S.-K. Adv. Synth. Catal. 2018; 360: 1544
- 14 For a review on the chemistry of acyl radicals, see: Chatgilialoglu C, Crich D, Komatsu M, Ryu I. Chem. Rev. 1999; 99: 1991
- 15a Jia F, Liu K, Xi H, Lu S, Li Z. Tetrahedron Lett. 2013; 54: 6337
- 15b Biswas P, Mandal S, Guin J. Org. Lett. 2020; 22: 4294
- 16a Wu T, Mu X, Liu G. Angew. Chem. Int. Ed. 2011; 50: 12578 ; Angew. Chem. 2011, 123, 12786
- 16b Mu X, Wu T, Wang H.-Y, Guo Y.-L, Liu G. J. Am. Chem. Soc. 2012; 134: 878
- 17 Seliverstova DV, Suslonov VV, Zarubaev VV, Trifonov RE. Russ. J. Org. Chem. 2018; 54: 633
- 18 Mai W.-P, Wang J.-T, Xiao Y.-M, Mao P, Lu K. Tetrahedron 2015; 71: 8041
- 19 Yuan Y.-Q, Kumar PS, Zhang C.-N, Yang M.-H, Guo S.-R. Org. Biomol. Chem. 2017; 15: 7330
- 20 Pan C, Chen C, Yu J.-T. Org. Biomol. Chem. 2017; 15: 1096
For reviews, see:
For reviews, see: