Citation: 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[J]. Chinese Chemical Letters, ;2021, 32(7): 2309-2312. doi: 10.1016/j.cclet.2021.02.025 shu

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

Liqiang Hao ^a ,
Hongyan Liu ^a ,
Zheng Zhang ^a ,
Fuqiang Wen ^a ,
Chengcai Xia ^{a, *,} ,
Zengfen Pang ^{b, *,}

a.
Institute of Pharmacology, Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Tai'an 271016, China
b.
Shandong Cancer Hospital and Institute, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan 250117, China

xiachc@163.com

pangzf0806@163.com

Received Date: 8 December 2020
Revised Date: 2 February 2021
Accepted Date: 9 February 2021
Available Online: 15 February 2021

Figures(5)

A novel route for tandem C–C/C–N formation, annulation and aromatization of hydrazones with 1, 2-dichloroethane to synthesize 1H-pyrazoles has been developed. Furthermore, the 1, 2-dichloroethane serves as alkylation reagent in good to excellent yields. This methodology features mild reaction conditions and good functional group tolerance, providing a direct approach for the preparation of 1H-pyrazoles.
- Tandem,
- Hydrazones,
- 1, 2-Dichloroethane,
- 1H-pyrazoles,
- Annulation
1. [1]
  T.G. Le, A. Kundu, A. Ghoshal, et al., J. Med. Chem. 62 (2019) 3367-3380. doi: 10.1021/acs.jmedchem.8b01790
2. [2]
  J. Carpenter, Y. Wang, G. Wu, et al., J. Med. Chem. 60 (2017) 6166-6190. doi: 10.1021/acs.jmedchem.7b00385
3. [3]
  J.C.C. Dallagnol, E. Khajehali, E.T. van Der Westhuizen, et al., J. Med. Chem. 61 (2018) 2875-2894. doi: 10.1021/acs.jmedchem.7b01812
4. [4]
  S. Varghese, R. Rahmani, S. Russell, et al., ACS Med. Chem. Lett. 11 (2020) 278-285. doi: 10.1021/acsmedchemlett.9b00218
5. [5]
  F. Chimenti, A. Bolasco, F. Manna, et al., Chem. Biol. Drug Des. 67 (2006) 206-214. doi: 10.1111/j.1747-0285.2006.00367.x
6. [6]
  L.L. De Oliveira, R.R. Campedelli, M.C.A. Kuhn, J.F. Carpentier, O.L. Casagrande, J. Mol. Catal. A Chem. 288 (2008) 58-62. doi: 10.1016/j.molcata.2008.03.020
7. [7]
  (a) S. Peruncheralathan, T.A. Khan, H. Ila, H. Junjappa, J. Org. Chem. 70 (2005) 10030-10035;
  (b) C.M. Thompson, J.L. Poole, J.L. Cross, I. Akritopoulou-Zanze, S.W. Djuric, Molecules 16 (2011) 9161-9177;
  (c) G.W. Zhang, Y. Zhao, H.B. Ge, Angew. Chem. Int. Ed. 52 (2013) 2559-2563;
  (d) F. Punner, Y. Sohtome, M. Sodeoka, Chem. Commun. (Camb. ) 52 (2016) 14093-14096;
  (e) J. Chen, R. Properzi, D.P. Uccello, et al., Org. Lett. 16 (2014) 4146-4149;
  (f) J.D. Kirkham, S.J. Edeson, S. Stokes, J.P.A. Harrity, Org. Lett. 14 (2012) 5354-5357;
  (g) J. Schranck, X.F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 18 (2012) 4827-4831.
8. [8]
  J. Comas-Barcel, R.S. Foster, B. Fiser, E. Gomez-Bengoa, J.P.A. Harrity, Chem. Eur. J. 20 (2014) 1-8. doi: 10.1002/chin.201527170
9. [9]
  N. Panda, A.K. Jena, J. Org. Chem. 77 (2012) 9401-9406. doi: 10.1021/jo301770k
10. [10]
  G.D. Wang, J. Sun, K. Wang, et al., Org. Chem. Front. 6 (2019) 1608-1612. doi: 10.1039/c9qo00367c
11. [11]
  L.Q. Hao, G.D. Wang, J. Sun, et al., Adv. Synth. Catal. 362 (2020) 1657-1662. doi: 10.1002/adsc.201901563
1. [1]
  Pei Ming Gu , Yu Ming Zhao , Yong Qiang Tu , Min Wang , Shu Yu Zhang . An alternative synthetic approach towards erythrinan and homoerythrinan alkaloids by tandem semipinacol/intramolecular Schmidt reaction. Chinese Chemical Letters, 2007, 18(8): 917-919. doi: 10.1016/j.cclet.2007.05.029
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Ju Lin LIU , Pei Hua MA , Guan Cheng CHEN . PRODUCTION OF VINYL CHLORIDE IN THE INFRARED LASER INDUCED PHOTOSENSITIZED CHAIN REACTION OF 1, 2-DICHLOROETHANE. Chinese Chemical Letters, 1990, 1(1): 29-30.
10. [10]
  Zheng Limeng , Shi Dongdong , Bao Hanyang , Liu Yunkui . Copper(0)/Selectfluor System-Catalyzed Tandem Annulation/ Aromatization of o-Aryl Benzenesulfonylimides: A Facile Synthesis of 6H-Phenanthridines. Chinese Journal of Organic Chemistry, 2019, 39(10): 2821-2828. doi: 10.6023/cjoc201904058
11. [11]
  Xiao Quan LU , Li Na HU , Xiao Qiang WANG , Jing CHEN . Study of Electron Transfer Reactions Between a Water/1,2-Dichloroethane Interface by Scanning Electrochemical Microscopy. Chinese Chemical Letters, 2004, 15(12): 1461-1464.
12. [12]
  Chuan Wei YAN , Xiang Qin LIN , Hai Chao LIN , Chu Nan CAO . Axial Coordination Effects of Pyridine on the Electrochemistry of (TPP)Co in 1,2-Dichloroethane Solution. Chinese Chemical Letters, 1997, 8(10): 905-908.
13. [13]
  Tong Lang , Mao Zhifeng , Tang Xiangzheng , Zhang Xuejing , Yan Ming . Cycloaddition of hydrazones and 1, 2-diarylalkynes promoted by t-BuOK/DMF: A convenient synthesis of tetraarylpyrazoles. Chinese Chemical Letters, 2019, 30(2): 395-397. doi: 10.1016/j.cclet.2018.06.018
14. [14]
  Hai Ying HE , Chen Lin , Cheng Xue ZHAO , Xi Kui JIANG . Dual-parameter Correlation Analysis of the Redox Potential Data of 1-Methyl-2-formyl-5-substituted Pyrroles and their Hydrazones. Chinese Chemical Letters, 2001, 12(12): 1097-1100.
15. [15]
  Roderick Hat Ying HE , Xi Kui JIANG . Dual-parameter Correlation Analysis of the Fluorescence Data of 1-Methyl-2-formyl-5-substituted Pyrrole(4-nitrophenyl)hydrazones. Chinese Chemical Letters, 1999, 10(6): 499-502.
16. [16]
  Huan Li , Yuxuan Han , Zi Yang , Zhenyu Yao , Lianhui Wang , Xiuling Cui . Rh(Ⅲ)-catalyzed annulation of azobenzenes and α-Cl ketones toward 3-acyl-2H-indazoles. Chinese Chemical Letters, 2021, 32(5): 1709-1712. doi: 10.1016/j.cclet.2020.12.027
17. [17]
  Yang Wulin , Wang Hao , Pan Zirong , Li Zhong , Deng Weiping . Asymmetric synthesis of pyrrolo[1, 2-a]indoles via organocatalytic[3 + 2] annulation of substituted 2-vinylindoles with azlactones. Chinese Chemical Letters, 2020, 31(3): 721-724. doi: 10.1016/j.cclet.2019.09.008
18. [18]
  Yang Mei , Cao Shixuan , He Zhengjie . Phosphine-Catalyzed[4+1] Annulation of Salicyl Imines with Maleimides and Synthesis of Spiro[benzofuran-2, 3'-pyrrolidine] Derivatives. Chinese Journal of Organic Chemistry, 2019, 39(8): 2235-2242. doi: 10.6023/cjoc201904041
19. [19]
  Hao Yongjia , Gong Yi , Cao Zhongyan , Zhou Ying , Zhou Jian . A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1, 4-di-thiane-2, 5-diol. Chinese Chemical Letters, 2020, 31(3): 681-684. doi: 10.1016/j.cclet.2019.08.018
20. [20]
  Duan Cong , Ye Ling , Xu Wenqin , Li Xinying , Chen Feng , Zhao Zhigang , Li Xuefeng . Organocatalytic cascade 1, 6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes. Chinese Chemical Letters, 2018, 29(8): 1273-1276. doi: 10.1016/j.cclet.2017.11.044

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(6)
HTML views(0)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142