Citation: Li Yubo, Zhao Yunhui, Luo Mingjian, Tang Zilong, Cao Chaotun, Deng Keqin. Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2504-2509. doi: 10.6023/cjoc201604031 shu

Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes

1.
Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education of China, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Corresponding author: Zhao Yunhui, zhao_yunhui@163.com Tang Zilong, zltang67@aliyun.com
Received Date: 14 April 2016
Revised Date: 20 May 2016

Fund Project: Project supported by the National Natural Science Foundation of China Nos.21372070, 21471052the Hunan Provincial Education Office Scientific Research Foundation Project No.14k035

Figures(4)

The isoquinoline and dihydroisoquinoline ring systems are found as the core nucleus in a wide variety of natural products and pharmaceutical agents with good biologically activity. Isoquinoline, benzoxazine-fused isoquinlines and pyrazo-lo[5,1-a]isoquinolines are prepared from o-alkynyl aldehydes and nitrogen-containing compounds via tandem reactions catalyzed by CuI or AgNO₃. The reactions have some advantages, such as mild reaction conditions, simple operation and easily available catalysts.
- isoquinoline,
- benzoxazine-fused isoquinlines,
- pyrazolo[5,1-a]isoquinolines,
- o-alkynyl aldehydes,
- tandem reaction
1. [1]
  Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341. (c) Inoue, K.; Kulsum, U.; Chowdhury, S. A.; Fujisawa, S. I.; Ishihara, M.; Yokoe I.; Sakagami, H. Anticancer Res. 2005, 25, 4053. (d) Su, S.; Porco Jr., J. A. Org. Lett. 2007, 9, 4983.
2. [2]
  Wada, Y.; Nishida, N.; Kurono, N.; Ohkuma, T.; Orito, K. Eur. J. Org. Chem. 2007, 4320. (b) Sun, Y.; Xun, K.; Wang Y.; Chen, X. Anti-Cancer Drugs 2009, 20, 757. (c) Wong, N. C. W.; Tucker, J. E. L.; Hansen, H. C.; Chiacchia, F. S.; McCaffrey, D. US 2008188467, 2008,[Chem. Abstr. 2008, 149, 246409].
3. [3]
  Liu, S.-J.; Zhao, Q.; Chen, R.-F.; Deng, Y.; Fan, Q.-L.; Li, F.-Y.; Wang, L.-H.; Huang, C.-H.; Huang, W. Chem. Eur. J. 2006, 12, 4351. (b) Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C. Inorg. Chem. 2006, 45, 6152. (c) Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.; Takiguchi, T.; Okada, S.; Hoshino, M.; Ueno, K. J. Am. Chem. Soc. 2003, 125, 12971.
4. [4]
5. [5]
  Sotomayor, N.; Dominguez, E. J. Org. Chem. 1996, 61, 4062. (b) Ishikawa, T.; Shimooka, K.; Narioka, T.; Noguchi, S.; Saito, T.; Ishikawa, A.; Yamazaki, E.; Harayama, T.; Seki, H.; Yamaguchi, K. J. Org. Chem. 2000, 65, 9143.
6. [6]
  Boudou, M.; Enders, D. J. Org. Chem. 2005, 70, 9486. (b) Walker, E. R.; Leung, S. Y.; Barrett, A. G. M. Tetrahedron Lett. 2005, 46, 6537.
7. [7]
  Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797. (b) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 341. (c) Youn, S. W. J. Org. Chem. 2006, 71, 2521.
8. [8]
  Maassarani, F.; Pfeffer, M.; Le Borgne, G. J. Chem. Soc., Chem. Commun. 1987, 8, 565.
9. [9]
  Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238.
10. [10]
  Girling, I. R.; Widdowson, D. A. Tetrahedron Lett. 1982, 23, 4281.
11. [11]
  Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (b) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980. (c) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877. (d) Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759. (e) Korivi, R. P.; Cheng, C.-H. Org. Lett. 2005, 7, 5179. (f) Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761. (g) Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131, 12886. (h) Florentino, L.; Aznar, F.; Valdés, C. Org. Lett. 2012, 14, 2323. (i) Li, C.; An, S.; Zhu, Y.; Zhang, J.; Kang, Y.; Liu, P.; Wang, Y.; Li, J. RSC Adv. 2014, 4, 49888.
12. [12]
  Chen, Z.; Yang, X.; Wu, J. Chem. Commun. 2009, 3469. (b) Chen, Z.; Ding, Q.; Yu, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 1692. (c) Liu, G.; Liu, H.; Qiu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 7049.
13. [13]
  Niu, Y.-N.; Yan, Z.-Y.; Gao, G.-L.; Wang, H.-L.; Shu, X.-Z.; Ji, K.-G.; Liang, Y.-M. J. Org. Chem. 2009, 74, 2893.
14. [14]
  Hwang S.; Lee, Y.; Lee, P.; Shin, S. Tetrahedron Lett. 2009, 50, 2305.
15. [15]
  Kobayashi, M.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2007, 48, 7019.
16. [16]
  Yu, X.; Yang, Q.; Lou, H.; Peng, Y.; Wu, J. Org. Biomol. Chem. 2011, 9, 7033.
17. [17]
  Zhao, Y.-H.; Li, Y.; Guo, T.; Tang, Z.; Deng, K.; Zhao, G. Synth. Commun. 2016, 46, 355. (b) Zhao, Y.-H.; Li, Y.; Guo, T.; Tang, Z.; Xie, W.; Zhao, G. Tetrahedron Lett. 2016, 57, 2257.
1. [1]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
2. [2]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
3. [3]
  Mengyun Wu , Yuxin Deng , Wenhui Wang , Dongdong Xu , Langui Xie , Peipei Sun . 电化学合成4-氯-2-三异丙基硅基喹啉. University Chemistry, 2026, 41(5): 222-229. doi: 10.12461/PKU.DXHX202511044
4. [4]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
5. [5]
  Yuanyuan Zeng , Xiaoti Chang , Jingru Li , Qilin Wang . 骨架编辑策略：异喹啉到2-氨基-1-萘甲醛的转化. University Chemistry, 2026, 41(10): 309-315. doi: 10.12461/PKU.DXHX202510028
6. [6]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
7. [7]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
8. [8]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
9. [9]
  Yinuo Wang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation. University Chemistry, 2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077
10. [10]
  Haolin Yang , Aoxiang Fan , Yi Song , Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156
11. [11]
  Wei LI , Jianjie XU , Linlin WANG , Chuanbing HOU , Hongliang HAN , Qionghua JIN . Synthesis, structure, and photocatalytic properties of {PMo₁₂}-based rare-earth tetraisopropyl ethylenediphosphonate complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2077-2091. doi: 10.11862/CJIC.20260220
12. [12]
  Xian BI , Sisi WANG , Jinyue ZHANG , Yujia PENG , Zhen SHEN , Hua LU . Discovery, development, and perspectives of circularly polarized luminescent materials based on β-isoindigo skeletons. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1049-1057. doi: 10.11862/CJIC.20240456
13. [13]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
14. [14]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
15. [15]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
16. [16]
  Chenxu Gong , Weizhen Wang , Ruiying Zhang , Wenfeng Wang , Yuanming Li , Yaofeng Yuan , Keyin Ye . Computational Chemistry-Assisted Organic Structure Analysis (CCAOSA): A Case Study of Propeller-Shaped Hexabenzotriphenylene. University Chemistry, 2026, 41(4): 438-446. doi: 10.12461/PKU.DXHX202503076
17. [17]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
18. [18]
  Guanghui Wang , Chen Qian , Zhiyong Ma . Preparation and Characterization of 7H-Benzo[C]Carbazole Based Ultra-Long Organic Room Temperature Phosphorescence Material. University Chemistry, 2025, 40(11): 289-299. doi: 10.12461/PKU.DXHX202412062
19. [19]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
20. [20]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2274)
HTML views(382)

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