Citation: Jian-Guo Yang, Ling-Zhen Xu, Ling Huang, Jian-Rong Gao, Miao-Chang Liu, Fu-You Pan, Ding-Ben Chen. Iron-catalyzed synthesis of polycyclic-fused azo[l,2-a]indolones via an S_NAr/acylation cascade reactions[J]. Chinese Chemical Letters, ;2016, 27(03): 340-344. doi: 10.1016/j.cclet.2015.11.005 shu

Iron-catalyzed synthesis of polycyclic-fused azo[l,2-a]indolones via an S_NAr/acylation cascade reactions

a.
a. College of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China;
b.
b. College of Chemical Engineering and Materials, Zhejiang University of Technology, Hangzhou 310014, China;
c.
c. Faculty of Chemistry & Material Engineering, Wenzhou University, Wenzhou 325027, China

Corresponding author: Jian-Guo Yang, Ding-Ben Chen,
Fund Project:

An efficient method has been developed for the cascade synthesis of azo[l,2-a]indolones from azoles and 2-fluoroaldehydes based on an iron-catalyzed S_NAr and a direct acylation reaction. A number of azo[l,2-a] indolones containing different azole rings and substituents were obtained in good yields.
- Iron,
- Cyclization,
- Cascade reaction,
- Azo[l,2-a]indol-ones,
- Direct acylation
1. [1]
  [1] (a) K. Fagnou, M. Lautens, A rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds, Chem. Rev. 103(2003) 169-196;
2. [2]
  (b) V. Ritleng, C. Sirlin, M. Pfeffer, Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates:reactions and mechanistic aspects, Chem. Rev. 102(2002) 1731-1769;
3. [3]
  (c) B.M. Trost, D.F. Toste, A.B. Pinkerton, Non-metathesis ruthenium-catalyzed C-C bond formation, Chem. Rev. 101(2001) 2067-2096;
4. [4]
  (d) T.Y. Luh, M.K. Leung, K.T. Wong, Transition metal-catalyzed activation of aliphatic C-X bonds in carbon-carbon bond formation, Chem. Rev. 100(2000) 3187-3204.
5. [5]
  [2] For reviews, see:(a) M Shibasaki, M. Kanai, Asymmetric synthesis of tertiary alcohols and α-tertiary amines via Cu-catalyzed C-C bond formation to ketones and ketimines, Chem. Rev. 108(2008) 2853-2873;
6. [6]
  (b) C. Bolm, J. Legros, J.L. Paih, L. Zani, (Ⅰ)ron-catalyzed reactions in organic synthesis, Chem. Rev. 104(2004) 6217-6254;
7. [7]
  (c) D.D. Díaz, P.O. Miranda, J.(Ⅰ). Padron, V.S. Martín, Recent uses of iron (Ⅲ) chloride in organic synthesis, Curr. Org. Chem. 10(2006) 457-476;
8. [8]
  (d) C.L. Sun, B.J. Li, Z.J. Shi, Direct C-H transformation via iron catalysis, Chem. Rev. 111(2011) 1293-1314.
9. [9]
  [3] (a) W.D. Jones, G.P. Foster, J.M. Putinas, The catalytic activation and functionalization of carbon-hydrogen bonds. Aldimine formation by the insertion of isonitriles into aromatic carbon-hydrogen bonds, J. Am. Chem. Soc. 109(1987) 5047-5048;
10. [10]
  (b) Z.P. Li, R. Yu, H. Li, (Ⅰ)ron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms, J. Angew. Chem. (Ⅰ)nt. Ed. 47(2008) 7497-7500;
11. [11]
  (c) Z.P. Li, L. Cao, C. Li, FeCl₂-catalyzed selective C-C bond formation by oxidative activation of a benzylic C-H bond, J. Angew. Chem. (Ⅰ)nt. Ed. 46(2007) 6505-6507;
12. [12]
  (d) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, (Ⅰ)ron-catalyzed direct arylation through directed C-H bond activation, J. Am. Chem. Soc. 130(2008) 5858-5859.
13. [13]
  [4] (a) C. Bolm, J. Legros, P.J. Le, L. Zani, (Ⅰ)ron-catalyzed reactions in organic synthesis, Chem. Rev. 104(2004) 6217-6254;
14. [14]
  (b) (Ⅰ). Bauer, H.J. Knölker, (Ⅰ)ron catalysis in organic synthesis, Chem. Rev. 115(2015) 3170-3387;
15. [15]
  (c) C.F. Lee, Y.C. Liu, S.S. Badsara, Transition-metal-catalyzed C-S bond coupling reaction, Chem. Asian J. 9(2014) 706-722.
16. [16]
  [5] (a) W. Jones, F. Fehe, Comparative reactivities of hydrocarbon carbon-hydrogen bonds with a transition-metal complex, Acc. Chem. Res. 22(1989) 91-100;
17. [17]
  (b) J.A. Labinger, J.E. Bercaw, Understanding and exploiting C-H bond activation, Nature 417(2002) 507-514;
18. [18]
  (c) K. Godula, D. Sames, C-H bond functionalization in complex organic synthesis, Science 312(2006) 67-72;
19. [19]
  (d) R.G. Bergman, Organometallic chemistry:C-H activation, Nature 446(2007) 391-393.
20. [20]
  [6] (a) J. Park, E. Park, A. Kim, et al., Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes:direct functionalization of the sp² C-H bond, Org. Lett. 13(2011) 4390-4393;
21. [21]
  (b) H. Wang, L.N. Guo, X.H. Duan, Decarboxylative acylation of cyclic enamides with α-oxocarboxylic acids by palladium-catalyzed C-H activation at room temperature, Org. Lett. 14(2012) 4358-4361;
22. [22]
  (c) W. Zhou, H.J. Li, L. Wang, Direct carbo-acylation reactions of 2-arylpyridines with α-diketones via Pd-Catalyzed C-H activation and selective C(sp²)-C(sp²) cleavage, Org. Lett. 14(2012) 4594-4597.
23. [23]
  [7] (a) J. Hu, E.A. Adogla, Y. Ju, D. Fan, Q. Wang, Copper-catalyzed ortho-acylation of phenols with aryl aldehydes and its application in one-step preparation of xanthones, Chem. Commun. 48(2012) 11256-11258;
24. [24]
  (b) J. Wang, C. Liu, J.W. Yuan, A.W. Lei, Copper-catalyzed oxidative coupling of alkenes with aldehydes:direct access to α,β-unsaturated ketones, Angew. Chem. (Ⅰ)nt. Ed. 52(2013) 2256-2259.
25. [25]
  [8] (a) S. Wertz, D. Leifert, A. Studer, Cross dehydrogenative coupling via basepromoted homolytic aromatic substitution (BHAS):synthesis of fluorenones and xanthones, Org. Lett. 15(2013) 928-931;
26. [26]
  (b) D. Leifert, C.G. Daniliuc, A. Studer, 6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS), Org. Lett. 15(2013) 6286-6289.
27. [27]
  [9] (a) D.B. Chen, G.D. Shen, W.L. Bao, An efficient cascade synthesis of various 2H-1,4-benzoxazin-3-(4H)-ones from o-halophenols and 2-halo-amides catalyzed by Cu(Ⅰ), Org. Biomol. Chem. 7(2009) 4067-4073;
28. [28]
  (b) D.B. Chen, Z.J. Wang, W.L. Bao, Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4] thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH₂, J.Org. Chem. 75(2010) 5768-5771;
29. [29]
  (c) D.B. Chen, W.L. Bao, An efficient domino synthesis of quinoxalin-2(1H)-ones via an S_NAr/coupling/demesylation reaction catalyzed by copper((Ⅰ)) as key step, Avd. Synth. Catal. 352(2010) 955-960;
30. [30]
  (d) D.B. Chen, J.S. Wu, J.G. Yang, et al., Cascade syntheses of aza[2,1-b][1,3]-benzothiazinone heteropolycyclic compounds from cyclic thiourea catalyzed by Cu((Ⅰ)), Tetrahedron Lett. 53(2012) 7104-7107;
31. [31]
  (e) D.B. Chen, Q.F. Chen, M.C. Liu, et al., Cascade synthesis of azoquinazolinones by Cu((Ⅰ))-catalyzed C-N coupling/C-H activation/C-N formation reactions under O₂, Tetrahedron 69(2013) 6461-6467.
32. [32]
  [10] J. Rosevear, J.E.K. Wilshire, Cyclization reactions in azole chemistry:the reaction of some azoles with o-fluoroacetophenone, o-fluorobenzaldehyde and o-fluorobenzophenone, Aust. J. Chem. 44(1991) 1097-1114.
33. [33]
  [11] (a) J.Y. Yang, C.Y. Dong, H.Y. Li, H.F. Li, Y.Z. Li, (Ⅰ)ron-catalyzed one-pot reactions of o-aryloxybenzaldehydes to xanthones, Chin. Sci. Bull. 57(2012) 2364-2367;
34. [34]
  (b) K. Paul, K. Bera, S. Jalal, S. Sarkar, U. Jana, Fe-catalyzed novel domino isomerization/cyclodehydration of substituted 2-[((Ⅰ)ndoline-3-ylidene)(methyl)]-benzaldehyde derivatives:an efficient approach toward benzo[b]carbazole derivatives, Org. Lett. 16(2014) 2166-2169.
1. [1]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
4. [4]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
5. [5]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
6. [6]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
7. [7]
  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
8. [8]
  Ting Pan , Dinghu Zhang , Guomei You , Xiaoxia Wu , Chenguang Zhang , Xinyu Miao , Wenzhi Ren , Yiwei He , Lulu He , Yuanchuan Gong , Jie Lin , Aiguo Wu , Guoliang Shao . PD-L1 targeted iron oxide SERS bioprobe for accurately detecting circulating tumor cells and delineating tumor boundary. Chinese Chemical Letters, 2025, 36(1): 109857-. doi: 10.1016/j.cclet.2024.109857
9. [9]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
10. [10]
  Xinyu Guo , Chang Li , Wenjun Deng , Yi Zhou , Yan Chen , Yushuang Xu , Rui Li . Phase engineering and heteroatom incorporation enable defect-rich MoS₂ for long life aqueous iron-ion batteries. Chinese Chemical Letters, 2025, 36(3): 109715-. doi: 10.1016/j.cclet.2024.109715
11. [11]
  Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012
12. [12]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
13. [13]
  Zhongsen Wang , Lijun Qiu , Yunhua Huang , Meng Zhang , Xi Cai , Fanyu Wang , Yang Lin , Yanbiao Shi , Xiao Liu . Alcohothermal synthesis of sulfidated zero-valent iron for enhanced Cr(Ⅵ) removal. Chinese Chemical Letters, 2024, 35(7): 109195-. doi: 10.1016/j.cclet.2023.109195
14. [14]
  Jiangshan Xu , Weifei Zhang , Zhengwen Cai , Yong Li , Long Bai , Shaojingya Gao , Qiang Sun , Yunfeng Lin . Tetrahedron DNA nanostructure/iron-based nanomaterials for combined tumor therapy. Chinese Chemical Letters, 2024, 35(11): 109620-. doi: 10.1016/j.cclet.2024.109620
15. [15]
  Xianzheng Zhang , Yana Chen , Zhiyong Ye , Huilin Hu , Ling Lei , Feng You , Junlong Yao , Huan Yang , Xueliang Jiang . Magnetic field-assisted microbial corrosion construction iron sulfides incorporated nickel-iron hydroxide towards efficient oxygen evolution. Chinese Journal of Structural Chemistry, 2024, 43(1): 100200-100200. doi: 10.1016/j.cjsc.2023.100200
16. [16]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
17. [17]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
18. [18]
  Yanan Zhou , Li Sheng , Lanlan Chen , Wenhua Zhang , Jinlong Yang . Axial coordinated iron-nitrogen-carbon as efficient electrocatalysts for hydrogen evolution and oxygen redox reactions. Chinese Chemical Letters, 2025, 36(1): 109588-. doi: 10.1016/j.cclet.2024.109588
19. [19]
  Yunlong Li , Xinyu Zhang , Shuang Liu , Chunsheng Li , Qiang Wang , Jin Ye , Yong Lu , Jiating Xu . Engineered iron-based metal-organic frameworks nanoplatforms for cancer theranostics: A mini review. Chinese Chemical Letters, 2025, 36(2): 110501-. doi: 10.1016/j.cclet.2024.110501
20. [20]
  Cheng-Shuang Wang , Bing-Yu Zhou , Yi-Feng Wang , Cheng Yuan , Bo-Han Kou , Wei-Wei Zhao , Jing-Juan Xu . Bifunctional iron-porphyrin metal-organic frameworks for organic photoelectrochemical transistor gating and biosensing. Chinese Chemical Letters, 2025, 36(3): 110080-. doi: 10.1016/j.cclet.2024.110080

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(674)
HTML views(24)

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

Iron-catalyzed synthesis of polycyclic-fused azo[l,2-a]indolones via an SNAr/acylation cascade reactions

Metrics

通讯作者: 陈斌, bchen63@163.com

Iron-catalyzed synthesis of polycyclic-fused azo[l,2-a]indolones via an S_NAr/acylation cascade reactions