Citation: Zhi-Wei Chen, Na Zhang, Zhi-Hua Wang, Wei-Ke Su. An efficient synthesis of novel chromeno[3’, 4’：5, 6]pyrano[2, 3-b]indole derivatives[J]. Chinese Chemical Letters, ;2013, 24(3): 199-201. shu

An efficient synthesis of novel chromeno[3’, 4’：5, 6]pyrano[2, 3-b]indole derivatives

1.
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China

Corresponding author: Wei-Ke Su,
Received Date: 6 November 2012
Available Online: 4 January 2013

An efficient two-step method was described for the synthesis of chromeno[3',4':5,6]pyrano[2,3-b]indole derivatives. The three-component reaction of 4-hydroxycoumarin, variously substituted benzaldehydes and indolin-2-one was promoted by P₂O₅ in refluxing ethanol to give trimolecular adducts, which were then cyclized in 1,2-dichloroethane under reflux using POCl₃.
- Pyranochromene,
- Indolin-2-one,
- 4-Hydroxycoumarin,
- Multicomponent reaction,
- Intramolecular cyclization
1. [1]
  [1] C. Kalinski, H. Lemoine, J. Schmidt, et al., Multicomponent reactions as a powerful tool for generic drug synthesis, Synthesis 24 (2008) 4007-4011.
2. [2]
  [2] Z.Q. Xu, K. Pupek, W.J. Suling, et al., Pyranocoumarin, a novel anti-TB pharmacophore: synthesis and biological evaluation against Mycobacterium tuberculosis, Bioorg. Med. Chem. 14 (2006) 4610-4626.
3. [3]
  [3] W.F. Fong, X.L. Shen, C. Globisch, et al., Methoxylation of 3',4'-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7,8-pyranocoumarin against cancer cells, Bioorg. Med. Chem. 16 (2008) 3694-3703.
4. [4]
  [4] C.R. Su, S.F. Yeh, C.M. Liu, et al., Anti-HBV and cytotoxic activities of pyranocoumarin derivatives, Bioorg. Med. Chem. 17 (2009) 6137-6143.
5. [5]
  [5] B. Kongkathip, N. Kongkathip, A. Sunthitikawinsakul, et al., Anti-HIV-1 constituents from Clausena excavate: Part Ⅱ. Carbazoles and a pyranocoumarin, Phytother. Res. 19 (2005) 728-731.
6. [6]
  [6] J.M. Khurana, B. Nand, P. Saluja, DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b] pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium, Tetrahedron 66 (2010) 5637-5641.
7. [7]
  [7] J. Zheng, Y.Q. Li, Basic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenes, Mendeleev Commun. 21 (2011) 280-281.
8. [8]
  [8] Z.W. Chen, Q. Zhu, W.K. Su, A novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water, Tetrahedron Lett. 52 (2011) 2601-2604.
9. [9]
  [9] W.W. Ma, X. Wang, F.L. Yan, et al., Reusable melamine trisulfonic acid-catalyzed three-component synthesis of 7-alkyl-6H,7H-naphtho[1',2':5,6]pyrano[3,2-c] chromen-6-ones, Monatsh. Chem. 142 (2011) 163-167.
10. [10]
  [10] Z.W. Chen, W.K. Su, J.H. Bi, Preparation of 7,12-dihydro-6H-chromeno[4,3-b] quinoline coumarin-like derivatives as antitumor agents, CN102584841A (18 July 2012).
11. [11]
  [11] Z.W. Chen, J.H. Bi, W.K. Su, A novel method for one-pot synthesis of furo[3,2-c] coumarin derivatives form 4-hydroxycoumarin and arylglyoxal under microwave irradiation, Chin. J. Chem. 30 (2012) 1845-1850.
12. [12]
  [12] Y. Jacquot, B. Refouvelet, L. Bermont, et al., Synthesis and cytotoxic activity of new 2,4-diaryl-4H,5H-pyrano[3,2-c]benzopyran-5-ones on MCF-7 cells, Pharmazie 57 (2002) 233-237.
13. [13]
  [13] K.C. Nicolaou, J.L. Hao, M.V. Reddy, et al., Chemistry and biology of diazonamide A: second total synthesis and biological investigations, J. Am. Chem. Soc. 126 (2004) 12897-12906.
14. [14]
  [14] I.M. EL-Deen, F.F. Mahmoud, Synthesis and chemical behavior of 2-chloro-3-(20-thienoylmethyl)quinoxaline towards some nucleophilic reagents, Phosphorus, Sulfur, Silicon Relat. Elem. 165 (2000) 205-212.
1. [1]
  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
2. [2]
  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
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]
  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]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
7. [7]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
8. [8]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
9. [9]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
10. [10]
  Jin Long , Xingqun Zheng , Bin Wang , Chenzhong Wu , Qingmei Wang , Lishan Peng . Improving the electrocatalytic performances of Pt-based catalysts for oxygen reduction reaction via strong interactions with single-CoN₄-rich carbon support. Chinese Chemical Letters, 2024, 35(5): 109354-. doi: 10.1016/j.cclet.2023.109354
11. [11]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
12. [12]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
13. [13]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
14. [14]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
15. [15]
  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
16. [16]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
17. [17]
  Junan Pan , Xinyi Liu , Huachao Ji , Yanwei Zhu , Yanling Zhuang , Kang Chen , Ning Sun , Yongqi Liu , Yunchao Lei , Kun Wang , Bao Zang , Longlu Wang . The strategies to improve TMDs represented by MoS₂ electrocatalytic oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(11): 109515-. doi: 10.1016/j.cclet.2024.109515
18. [18]
  Hailang Deng , Abebe Reda Woldu , Abdul Qayum , Zanling Huang , Weiwei Zhu , Xiang Peng , Paul K. Chu , Liangsheng Hu . Killing two birds with one stone: Enhancing the photoelectrochemical water splitting activity and stability of BiVO₄ by Fe ions association. Chinese Chemical Letters, 2024, 35(12): 109892-. doi: 10.1016/j.cclet.2024.109892
19. [19]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
20. [20]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(659)
HTML views(18)

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