Electrooxidative [3 + 2] annulation of amidines with alkenes for the synthesis of spiroimidazolines
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* Corresponding authors.
E-mail addresses: duanjd@njtech.edu.cn (J. Duan), guok@njtech.edu.cn (K. Guo).
Citation:
Sai Zhang, Gaochen Xu, Huan Yan, Qinghuan Wu, Jingjing Meng, Jindian Duan, Kai Guo. Electrooxidative [3 + 2] annulation of amidines with alkenes for the synthesis of spiroimidazolines[J]. Chinese Chemical Letters,
;2022, 33(12): 5128-5131.
doi:
10.1016/j.cclet.2022.04.006
D.C. Kombo, A.A. Mazurov, J. Chewning, et al., Bioorg. Med. Chem. Lett. 22 (2012) 1179–1186.
doi: 10.1016/j.bmcl.2011.11.090
A. Dekeyne, M.J. Millan, Neuropharmacology 51 (2006) 718–726.
doi: 10.1016/j.neuropharm.2006.05.012
C.A. Bernhart, P.M. Perreaut, B.P. Ferrari, et al., J. Med. Chem. 36 (1993) 3371–3380.
doi: 10.1021/jm00074a018
S. Kato, T. Yoshino, M. Shibasaki, M. Kanai, S. Matsunaga, Angew. Chem. Int. Ed. 51 (2012) 7007–7010.
doi: 10.1002/anie.201203005
H. Cai, Y. Zhou, D. Zhang, J. Xu, H. Liu, Chem. Commun. 50 (2014) 14771–14774.
doi: 10.1039/C4CC06000H
M. Zhao, L. Jing, H. Zhou, M. Shi, RSC Adv. 5 (2015) 75648–75652.
doi: 10.1039/C5RA17075C
J. Ren, C. Pi, X. Cui, Y. Wu, Org. Lett. 23 (2021) 6628–6632.
doi: 10.1021/acs.orglett.1c02077
H. Liang, G. Li, L. Zhang, et al., Org. Lett. 23 (2021) 5821–5825.
doi: 10.1021/acs.orglett.1c01970
Y. Zhang, J. Kuang, X. Xiao, L. Wang, Y. Ma, Org. Lett. 23 (2021) 3960–3964.
doi: 10.1021/acs.orglett.1c01116
W. Liu, J. He, X. Liu, et al., J. Org. Chem. 85 (2020) 14954–14962.
doi: 10.1021/acs.joc.0c01715
C. Wang, Y. Yu, Z. Su, X. Li, H. Cao, Org. Lett. 21 (2019) 4420–4423.
doi: 10.1021/acs.orglett.9b00969
W. Liu, Y. Zhang, J. He, et al., J. Org. Chem. 84 (2019) 11348–11358.
doi: 10.1021/acs.joc.9b01818
D. Meng, Y. Xie, Q. Peng, J. Wang, Org. Lett. 22 (2020) 7635–7639.
doi: 10.1021/acs.orglett.0c02832
J. Li, M. John, L. Ackermann, Chem. Eur. J. 20 (2014) 5403–5408.
doi: 10.1002/chem.201304944
A. Chaskar, S. Pardeshi, P. Sathe, K. Vadagaonkar, Adv. Synth. Catal. 359 (2017) 4217–4226.
doi: 10.1002/adsc.201700900
Y. Li, Y. Fu, C. Ren, et al., Org. Chem. Front. 2 (2015) 1632–1636.
doi: 10.1039/C5QO00285K
P. Wu, J. Qu, Y. Li, et al., Adv. Synth. Catal. 357 (2015) 3868–3874.
doi: 10.1002/adsc.201500701
D. Tang, P. Wu, X. Liu, et al., J. Org. Chem. 78 (2013) 2746–2750.
doi: 10.1021/jo302555z
X. Liu, D. Wang, Y. Chen, D. Tang, B. Chen, Adv. Synth. Catal. 355 (2013) 2798–2802.
doi: 10.1002/adsc.201300590
X. Liu, D. Wang, B. Chen, Tetrahedron 69 (2013) 9417–9421.
doi: 10.1016/j.tet.2013.08.077
Y. Zhu, C. Li, J. Zhang, et al., Org. Lett. 17 (2015) 3872–3875.
doi: 10.1021/acs.orglett.5b01854
Z. Zhan, M. Zhang, P. Jiang, et al., Asian J. Org. Chem. 10 (2021) 1801–1813.
doi: 10.1002/ajoc.202100287
H. Xu, R. Hong, M. Weng, et al., Org. Lett. 23 (2021) 5305–5310.
doi: 10.1021/acs.orglett.1c01475
H. Xu, R. Huang, Z. Shu, R. Hong, Z. Zhang, Org. Biomol. Chem. 19 (2021) 4978–4985.
doi: 10.1039/d1ob00508a
H. Xu, K. Chen, H. Liu, G. Wang, Org. Chem. Front. 5 (2018) 2864–2869.
doi: 10.1039/c8qo00723c
S. Tang, Y. Liu, A. Lei, Chem 4 (2018) 27–45.
doi: 10.1016/j.chempr.2017.10.001
Y. Yuan, A. Lei, Nat. Commun. 11 (2020) 802.
doi: 10.1038/s41467-020-14322-z
Z. Yang, Y. Yua, L. Lai, et al., Green Synth. Catal. 2 (2021) 19–26.
doi: 10.1016/j.gresc.2021.01.009
Y. Yuan, A. Lei, Acc. Chem. Res. 52 (2019) 3309–3324.
doi: 10.1021/acs.accounts.9b00512
J.C. Siu, N. Fu, S. Lin, Acc. Chem. Res. 53 (2020) 547–560.
doi: 10.1021/acs.accounts.9b00529
M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319.
doi: 10.1021/acs.chemrev.7b00397
K. Jiao, Y. Xing, Q. Yang, H. Qiu, T. Mei, Acc. Chem. Res. 53 (2020) 300–310.
doi: 10.1021/acs.accounts.9b00603
R. Francke, R.D. Little, Chem. Soc. Rev. 43 (2014) 2492–2521.
doi: 10.1039/c3cs60464k
Y. Jiang, K. Xu, C. Zeng, Chem. Rev. 118 (2018) 4485–4540.
doi: 10.1021/acs.chemrev.7b00271
X. Chen, F. Xiao, W. He, Org. Chem. Front. 8 (2021) 5206–5228.
doi: 10.1039/d1qo00375e
C. Ma, P. Fang, Z. Liu, et al., Sci. Bull. 66 (2021) 2412–2429.
doi: 10.1016/j.scib.2021.07.011
J. Zhong, Y. Yu, D. Zhang, K. Ye, Chin. Chem. Lett. 32 (2021) 963–972.
doi: 10.1016/j.cclet.2020.08.011
Y. Yu, Y. Jiang, S. Wu, et al., Chin. Chem. Lett. 33 (2022) 2009–2014.
doi: 10.1016/j.cclet.2021.10.016
P. Xiong, H. Xu, Acc. Chem. Res. 52 (2019) 3339–3350.
doi: 10.1021/acs.accounts.9b00472
M.K. Kärkäs, Chem. Soc. Rev. 47 (2018) 5786–5865.
doi: 10.1039/c7cs00619e
C. Ma, P. Fang T. Mei, ACS Catal. 8 (2018) 7179–7189.
doi: 10.1021/acscatal.8b01697
T. Xiong, Q. Zhang, Chem. Soc. Rev. 45 (2016) 3069–3087.
doi: 10.1039/C5CS00852B
N. Dagar, P.P. Sen, S.R. Roy, ChemSusChem 14 (2021) 1229–1257.
doi: 10.1002/cssc.202002567
N. Chen, H. Xu, Green Synth. Catal. 2 (2021) 165–178.
doi: 10.1016/j.gresc.2021.03.002
Q. Yang, Y. Li, Y. Liu, et al., Org. Chem. Front. 8 (2021) 5410–5417.
doi: 10.1039/d1qo00959a
J. Chen, H. Wu, Q. Gui, et al., Org. Lett. 22 (2020) 2206–2209.
doi: 10.1021/acs.orglett.0c00387
C. Sun, F. Lian, K. Xu, C. Zeng, B. Sun, Adv. Synth. Catal. 361 (2019) 4041–4047.
doi: 10.1002/adsc.201900537
K. Liu, C. Song, J. Wu, et al., Green Chem. 21 (2019) 765–769.
doi: 10.1039/c8gc03786h
Z. Hou, Z. Mao, Y.Y. Melcamu, X. Lu, H. Xu, Angew. Chem. Int. Ed. 57 (2018) 1636–1639.
doi: 10.1002/anie.201711876
J.C. Siu, J.B. Parry, S. Lin, J. Am. Chem. Soc. 141 (2019) 2825–2831.
doi: 10.1021/jacs.8b13192
K. Hu, Y. Zhang, Z. Zhou, et al., Org. Lett. 22 (2020) 5773–5777.
doi: 10.1021/acs.orglett.0c01821
H. Wang, J. Shi, J. Tan, et al., Org. Lett. 21 (2019) 9430–9433.
doi: 10.1021/acs.orglett.9b03641
M. Zheng, X. Yuan, Y. Cui, et al., Org. Lett. 20 (2018) 7784–7789.
doi: 10.1021/acs.orglett.8b03191
C. Liu, Q. Jiang, Y. Lin, Z. Fang, K. Guo, Org. Lett. 22 (2020) 795–799.
doi: 10.1021/acs.orglett.9b04141
J. Duan, Y. Mao, L. Zhang, et al., Adv. Synth. Catal. 362 (2020) 695–699.
doi: 10.1002/adsc.201901333
Y. Wu, H. Yi, A. Lei, ACS Catal. 8 (2018) 1192–1196.
doi: 10.1021/acscatal.7b04137
Z. Ye, J. Gao, X. Duan, et al., Chem. Commun. 57 (2021) 8969–8972.
doi: 10.1039/d1cc03288g
X. Dong, R. Wang, W. Jin, C. Liu, Org. Lett. 22 (2020) 3062–3066.
doi: 10.1021/acs.orglett.0c00814
Y. Kurimoto, J. Yamashita, K. Mitsudo, E. Sato, S. Suga, Org. Lett. 23 (2021) 3120–3124.
doi: 10.1021/acs.orglett.1c00807
C. Cai, X. Shu, H. Xu, Nat. Commun. 10 (2019) 4953.
doi: 10.1038/s41467-019-13024-5
K. Hu, Y. Zhang, Z. Zhou, et al., Org. Lett. 22 (2020) 5773–5777.
doi: 10.1021/acs.orglett.0c01821
Xiaojian Ren , Qiang Liu , Zhixiang Wang , Xiangyu Chen . Visible-light-induced direct hydrodifluoromethylation of alkenes with difluoromethyltriphenylphosphonium iodide salt. Chinese Chemical Letters, 2023, 34(1): 107473-1-107473-4. doi: 10.1016/j.cclet.2022.04.071
Wang Guodong , Guo Yanhui , Wan Jieping . Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines. Chinese Journal of Organic Chemistry, 2020, 40(3): 645-650. doi: 10.6023/cjoc201912018
Changwei Chen , Sunliang Cui . BF3-promoted annulation of azonaphthalenes and ynamides for synthesis of benzo[e]indoles. Chinese Chemical Letters, 2021, 32(1): 421-424. doi: 10.1016/j.cclet.2020.04.010
Ping Zhang , Wenju Chang , Hongyun Jiao , Yanshang Kang , Wenxuan Zhao , Peipei Cui , Yong Liang , Wei-Yin Sun , Yi Lu . Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst. Chinese Chemical Letters, 2021, 32(5): 1717-1720. doi: 10.1016/j.cclet.2021.01.024
Deping Wang , Yan Liu , Linhua Wang , Hu Cheng , Yuming Zhang , Ge Gao . Synthesis of π-extended dibenzo[d, k]ullazines by a palladium-catalyzed double annulation using arynes. Chinese Chemical Letters, 2021, 32(4): 1407-1410. doi: 10.1016/j.cclet.2020.09.057
Yuncan Chen , Shan Lv , Ruizhi Lai , Yingying Xu , Xin Huang , Jianglian Li , Guanghui Lv , Yong Wu . Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas. Chinese Chemical Letters, 2021, 32(8): 2555-2558. doi: 10.1016/j.cclet.2021.02.052
Liqiang Hao , Hongyan Liu , Zheng Zhang , Fuqiang Wen , Chengcai Xia , Zengfen Pang . Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1, 2-dichloroethane. Chinese Chemical Letters, 2021, 32(7): 2309-2312. doi: 10.1016/j.cclet.2021.02.025
Yanhui Guo , Yunyun Liu , Jie-Ping Wan . Amine-catalyzed synthesis of N2-sulfonyl 1, 2, 3-triazole in water and the tunable N2-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation. Chinese Chemical Letters, 2022, 33(2): 855-858. doi: 10.1016/j.cclet.2021.08.003
Cao Weidi , Liu Xiaohua , Feng Xiaoming . Chiral organobases: Properties and applications in asymmetric catalysis. Chinese Chemical Letters, 2018, 29(8): 1201-1208. doi: 10.1016/j.cclet.2018.05.041
Zhi-Wei Chen , Jun-Bo Hou , Zhao-Ran Dai , Xiao-Feng Yang . A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation. Chinese Chemical Letters, 2016, 27(10): 1622-1625. doi: 10.1016/j.cclet.2016.04.009
Li Yao , Chen Kunquan , Zhang Yan , Sun Dequn , Ye Song . N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones. Chinese Chemical Letters, 2018, 29(8): 1209-1211. doi: 10.1016/j.cclet.2018.03.003
Han Xiang-Lei , Lin Peng-Peng , Li Qingjiang . Recent advances of allenes in the first-row transition metals catalyzed C—H activation reactions. Chinese Chemical Letters, 2019, 30(8): 1495-1502. doi: 10.1016/j.cclet.2019.04.027
Hui Zheng , Ying Han , Jing Sun , Chao-Guo Yan . Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate. Chinese Chemical Letters, 2021, 32(5): 1683-1686. doi: 10.1016/j.cclet.2020.12.024
Song Zou , Zeyu Zhang , Chao Chen , Chanjuan Xi . MeOTf-catalyzed formal [4 + 2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion. Chinese Chemical Letters, 2022, 33(6): 3021-3025. doi: 10.1016/j.cclet.2021.12.012
Shoudong Xie , Weinan Chen , Si Liu , Hao Zong , Binbin Ming , Gang Zhou . Facile synthesis and functionalization of fluoranthenes via intramolecular [4 + 2] annulations between thiophenes and alkynes. Chinese Chemical Letters, 2023, 34(6): 107642-1-107642-4. doi: 10.1016/j.cclet.2022.06.065
He Juan . The History of the Chinese Chemical Terms Wan, Xi and Que. Chemistry, 2016, 79(7): 667-670,666.
Xukai Zhou , Jiaqiong Sun , Xingwei Li . Chemo-selective couplings of anilines and acroleins/enones under substrate control and condition control. Chinese Journal of Catalysis, 2018, 39(11): 1782-1791. doi: 10.1016/S1872-2067(18)63134-1
WANG Zhen , LI En , HE Zhiqi , CHEN Jiean , HUANG Yong . Dehydrogenative Annulation of γ, δ-Unsaturated Amides and Alkynes via Double C―H Activation. Acta Physico-Chimica Sinica, 2019, 35(9): 906-912. doi: 10.3866/PKU.WHXB201811038
Yun Fa Zheng , Jian Yu , Guo Bing Yan , Xu Li , Song Luo . FeBr3-catalyzed dibromination of alkenes and alkynes. Chinese Chemical Letters, 2011, 22(10): 1195-1198. doi: 10.1016/j.cclet.2011.05.005
Wei Yuan HUANG , Han Zhong ZHNG . ORGANOPHOSPHINE INITIATED REACTION OF PERFLUOROALKYL IODIDES WITH ALKENES. Chinese Chemical Letters, 1990, 1(2): 153-154.