Citation: Hong-Kun Yang, Yuan-Feng Tong, Song Wu. A novel and efficient strategy involving a CuI catalyzed cascade reaction to synthesize acenaphtho[1,2-b]quinoline derivatives[J]. Chinese Chemical Letters, ;2016, 27(03): 349-352. doi: 10.1016/j.cclet.2015.11.011 shu

A novel and efficient strategy involving a CuI catalyzed cascade reaction to synthesize acenaphtho[1,2-b]quinoline derivatives

1.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China

Corresponding author: Song Wu,
Received Date: 9 October 2015
Available Online: 24 October 2015
Fund Project: We gratefully acknowledge the National Key Technology R&D Program "New Drug Innovation" of China (No.2013ZX09402103) (No.2013ZX09402103)

A novel and efficient approach for the straightforward synthesis of biologically significant acenaphtho[1,2-b]quinoline derivatives in good yields utilizing CuI as a catalyst with a broad array of substrates has been developed. The strategy features as a CuI-catalyzed cascade reaction involving the formation of two new C-C bonds and one new C-N bond with high atom economy. A proposed mechanism for the reaction is described.
- Cascade reaction,
- CuI,
- Substituted anilines,
- Phenylethynyl-1-naphthaldehydes,
- Acenaphtho[1,2-b]quinolones
1. [1]
  [1] K.W. Bentley, β-Phenylethylamines and the isoquinoline alkaloids, J. Nat. Prod. Rep. 22(2005) 249-268.
2. [2]
  [2] M. Chrzanowska, M.D. Rozwadowska, Asymmetric synthesis of isoquinoline alkaloids, Chem. Rev. 104(2004) 3341-3370.
3. [3]
  [3] K.W. Bentley, β-Phenylethylamines and the isoquinoline alkaloids, J. Nat. Prod. Rep. 23(2006) 444-463.
4. [4]
  [4] R.S. Keri, S.A. Patil, Quinoline:a promising antitubercular target, Biomed. Pharmacother. 68(2014) 1161-1175.
5. [5]
  [5] Y. Sheng, B. Sun, X. Xie, et al., DMH1(4-[6-(4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) inhibits chemo-therapeutic drug-induced autophagy, Acta Pharm. Sin. B 5(2015) 330-336.
6. [6]
  [6] B. Gryzlo, K. Kulig, Quinoline-a promising fragment in the search for new antimalarials, Mini-rev. Med. Chem. 14(2014) 332-344.
7. [7]
  [7] P. Zajdel, A. Partyka, K. Marciniec, et al., Quinoline-and isoquinoline-sulfonamide analogs of aripiprazole:novel antipsychotic agents? Future Med. Chem. 6(2014) 57-75.
8. [8]
  [8] S. Mukherjee, M. Pal, Quinolines:a new hope against inflammation, Drug Discov. Today 18(2013) 389-398.
9. [9]
  [9] K. Kaur, K.M. Jain, R.P. Reddy, R. Jain, Quinolines and structurally related heterocycles as antimalarials, Euro. J. Med. Chem. 45(2010) 3245-3264.
10. [10]
  [10] A.D.C. Parenty, L.V. Smith, K.M. Guthrie, et al., Highly stable phenanthridinium frameworks as a new class of tunable DNA binding agents with cytotoxic properties, J. Med. Chem. 48(2005) 4504-4506.
11. [11]
  [11] V.R. Solomon, H. Lee, Quinoline as a privileged scaffold in cancer drug discovery, Curr. Med. Chem. 18(2011) 1488-1508.
12. [12]
  [12] K. (Ⅰ)wasa, M. Moriyasu, Y. Tachibana, et al., Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-H(Ⅰ)V agents, Bioorg. Med. Chem. 9(2001) 2871-2884.
13. [13]
  [13] M.V. Reddy, M.R. Rao, D. Rhodes, et al., Lamellarin α 20-sulfate, an inhibitor of H(Ⅰ)V-1 integrase active against H(Ⅰ)V-1 virus in cell culture, J. Med. Chem. 42(2009) 1901-1907.
14. [14]
  [14] R. Khusnutdinov, A. Bayguzina, R. Aminov, U. Dzhemilev, Quinoline synthesis by the reaction of anilines with 1,2-diols catalyzed by iron compounds, J. Heterocycl. Chem. (2015), http://dx.doi.org/10.1002/jhet.2425.
15. [15]
  [15] X. Mi, J. Chen, L. Xu, FeCl₃-catalyzed SF₅-containing quinoline synthesis:threecomponent coupling reactions of SF₅-anilines, aldehydes and alkynes, Eur. J. Org. Chem. 2015(2015) 1415-1418.
16. [16]
  [16] C.H. Tseng, C.K. Lin, Y.L. Chen, et al., Synthesis, antiproliferative and anti-dengue virus evaluations of 2-aroyl-3-arylquinoline derivatives, Euro. J. Med. Chem. 79(2014) 66-76.
17. [17]
  [17] M.H. Son, J.Y. Kim, E.J. Lim, et al., Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain, Bioorg. Med. Chem. Lett. 23(2013) 1472-1476.
18. [18]
  [18] P. Szymanski, A. Laznickova, M. Laznicek, et al., 2,3-Dihydro-1H-cyclopenta[b]-quinoline derivatives as acetylcholinesterase inhibitors-synthesis, radiolabeling and biodistribution, (Ⅰ)nt. J. Mol. Sci. 13(2012) 10067-10090.
19. [19]
  [19] S.L. Schreiber, Target-oriented and diversity-oriented organic synthesis in drug discovery, Science 287(2000) 1964-1969.
20. [20]
  [20] C.J. O'Connor, H.S.G. Beckmann, D.R. Spring, Diversity-oriented synthesis:producing chemical tools for dissecting biology, Chem. Soc. Rev. 41(2012) 4444-4456.
21. [21]
  [21] L.Q. Lu, J.R. Chen, W.J. Xiao, Development of cascade reactions for the concise construction of diverse heterocyclic architectures, Acc. Chem. Res. 45(2012) 1278-1293.
22. [22]
  [22] J.M. Smith, J. Moreno, B.W. Boal, N.K. Garg, Cascade reactions:a driving force in akuammiline alkaloid total synthesis, Angew. Chem. (Ⅰ)nt. Ed. 54(2015) 400-412.
23. [23]
  [23] J.H. Xie, D.H. Bao, Q.L. Zhou, Recent advances in the development of chiral metal catalysts for the asymmetric hydrogenation of ketones, Synthesis 47(2015) 460-471.
24. [24]
  [24] E.G. Chepaikin, Oxidative functionalization of alkanes under dioxygen in the presence of homogeneous noble metal catalysts, J. Mol. Catal. A-Chem. 85(2014) 160-174.
25. [25]
  [25] N.T. Patil, A.K. Mutyala, G.V.V. Lakshmi, P.V.K. Raju, B. Sridhar, Facile assembly of fused isoquinolines by gold ((Ⅰ))-catalyzed coupling-cyclization reactions between o-alkynylbenzaldehydes and aromatic amines containing tethered nucleophiles, Eur. J. Org. Chem. 2010(2010) 1999-2007.
26. [26]
  [26] B. Jiang, Y. Zhou, Q. Kong, et al., ‘One-pot’ synthesis of dihydrobenzo[4,5][1,3] oxazino[2,3-a]isoquinolines via a silver ((Ⅰ))-catalyzed cascade approach, Molecules 18(2013) 814-831.
27. [27]
  [27] N.T. Patil, A. Konala, S. Sravanti, et al., Electrophile induced branching cascade:a powerful approach to access various molecular scaffolds and their exploration as novel anti-mycobacterial agents, Chem. Commun. 49(2013) 10109-10111.
28. [28]
  [28] A.K. Verma, D. Choudhary, R.K. Saunthwal, et al., On water:silver-catalyzed domino approach for the synthesis of benzoxazine/oxazine-fused isoquinolines and naphthyridines from o-alkynyl aldehydes, J. Org. Chem. 78(2013) 6657-6669.
29. [29]
  [29] Y.F. Tong, S.P. Wang, Q.Y. Yang, Synthesis of 8-iodo-1-naphthaldehyde, Chem. Reagent. 35(2013) 455-456(p.460).
30. [30]
  [30] L.K. Kong, Y.Y. Zhou, H. Huang, et al., Copper-catalyzed synthesis of substituted quinolines via C-N coupling/condensation from ortho-acylanilines and alkenyl iodides, J. Org. Chem. 80(2015) 1275-1278.
31. [31]
  [31] B. Li, C.H. Guo, X.S. Fan, J. Zhang, X.Y. Zhang, Synthesis of substituted quinoline via copper-catalyzed one-pot cascade reactions of 2-bromobenzaldehydes with aryl methyl ketones and aqueous ammonia, Tetrahedron Lett. 55(2014) 5944-5948.
32. [32]
  [32] S.B. Paul, K.C. Majumdar, S. Anwar, S. Choudhury, Copper((Ⅰ)) iodide supported synthesis of coumarin and quinolone annulated 2-aminothiazoles, Synlett 26(2015) 1039-1044.
33. [33]
  [33] H.C. Ouyang, R.Y. Tang, P. Zhong, Cu(Ⅰ)/(Ⅰ)₂-promoted electrophilic tandem cyclization of 2-ethynylbenzaldehydes with ortho-benzenediamines:synthesis of iodoisoquinoline-fused benzimidazoles, J. Org. Chem. 76(2011) 223-228.
1. [1]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
2. [2]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
3. [3]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
4. [4]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
5. [5]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
6. [6]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
7. [7]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
8. [8]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
9. [9]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
10. [10]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
11. [11]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
12. [12]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
13. [13]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
14. [14]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
15. [15]
  Huaran Zhang , Yuting Huang , Yingjie Tang , Dekun Kong , Yi Zou . Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type Ⅲ- polyketide pathway. Chinese Chemical Letters, 2024, 35(7): 108968-. doi: 10.1016/j.cclet.2023.108968
16. [16]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
17. [17]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
18. [18]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
19. [19]
  Jun Xiong , Ke-Ke Chen , Neng-Bin Xie , Wei Chen , Wen-Xuan Shao , Tong-Tong Ji , Si-Yu Yu , Yu-Qi Feng , Bi-Feng Yuan . Demethylase-assisted site-specific detection of N¹-methyladenosine in RNA. Chinese Chemical Letters, 2024, 35(5): 108953-. doi: 10.1016/j.cclet.2023.108953
20. [20]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(634)
HTML views(23)

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