RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2018; 50(16): 3243-3249
DOI: 10.1055/s-0036-1591589
DOI: 10.1055/s-0036-1591589
paper
Synthesis of Indolo[2,1-a]isoquinolines via Copper-Catalyzed C–C Coupling and Cyclization of 2-(2-Bromoaryl)-1H-indoles with 1,3-Diketones
This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1D1A1B03028226). P.D.Q.D. thanks Y. M. Park, Internal Medicine of Geoje Medical Center (Gyeongnam, Republic of Korea) for partial financial support during his stay in the Republic of Korea.Weitere Informationen
Publikationsverlauf
Received: 23. März 2018
Accepted after revision: 23. April 2018
Publikationsdatum:
12. Juni 2018 (online)
Abstract
2-(2-Bromoaryl)-1H-indoles are coupled and cyclized with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of copper(I) iodide along with a base to afford the corresponding indolo[2,1-a]isoquinolines in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591589.
- Supporting Information
-
References
- 1a Ambros R. von Angerer S. Wiegrebe W. Arch. Pharm. (Weinheim) 1988; 321: 481
- 1b Ambros R. von Angerer S. Wiegrebe W. Arch. Pharm. (Weinheim) 1988; 321: 743
- 1c Ambros R. Schneider MR. von Angerer S. J. Med. Chem. 1990; 33: 153
- 1d Goldbrunner M. Loidl G. Polossek T. Mannschreck A. von Angerer E. J. Med. Chem. 1997; 40: 3524
- 2 Morimoto K. Hirano K. Satoh T. Miura M. Org. Lett. 2010; 12: 2068
- 3a Harley-Mason J. J. Chem. Soc. 1953; 1465
- 3b Kametani T. Ogasawara K. J. Chem. Soc. C 1967; 2208
- 3c Boente JM. Castedo L. Rodriguez de Lera A. Saá JM. Suau R. Vidal MC. Tetrahedron Lett. 1983; 24: 2295
- 3d Orito K. Harada R. Uchiito S. Tokuda M. Org. Lett. 2000; 2: 1799
- 3e Kraus GA. Beasley J. Tetrahedron Lett. 2013; 54: 5597
- 4 Verma AK. Kesharwani T. Singh J. Tandon V. Larock RC. Angew. Chem. Int. Ed. 2009; 48: 1138
- 5 Mamane V. Hannen P. Fürstner A. Chem. Eur. J. 2004; 10: 4556
- 6 Sun H. Wang C. Yang Y.-F. Chen P. Wu YD. Zhang X. Huang Y. J. Org. Chem. 2014; 79: 11863
- 7a de Koning CB. Michael JP. Pathak R. van Otterlo WA. L. Tetrahedron Lett. 2004; 45: 1117
- 7b Lötter AN. C. Pathak R. Sello TS. Fernandes MA. van Otterlo WA. L. de Koning CB. Tetrahedron 2007; 63: 2263
- 8a Dao PD. Q. Lee HK. Sohn H.-S. Yoon NS. Cho CS. ACS Omega 2017; 2: 2953
- 8b Ho SL. Dao PD. Q. Cho CS. Synlett 2017; 28: 1811
- 9a For palladium-catalyzed synthesis of N-fused hybrid scaffolds, see: Yoo JM. Ho SL. Cho CS. Synlett 2016; 27: 1383
- 9b Yang BW. Ho SL. Lim H.-J. Cho CS. J. Organomet. Chem. 2016; 806: 83
- 10 Yang BW. Dao PD. Q. Yoon NS. Cho CS. J. Organomet. Chem. 2017; 851: 136
- 11 Ho SL. Cho CS. Sohn H.-S. Synthesis 2015; 47: 216
- 12 Xie X. Cai G. Ma D. Org. Lett. 2005; 7: 4693
- 13a Fan X. He Y. Cui L. Guo S. Wang J. Zhang X. Eur. J. Org. Chem. 2012; 673
- 13b Kavala V. Wang C.-C. Barange DK. Kuo C.-W. Lei P.-O. Yao C.-F. J. Org. Chem. 2012; 77: 5022
- 14a Cai S. Wang F. Xi C. J. Org. Chem. 2012; 77: 2331
- 14b Yip SF. Cheung HY. Zhou Z. Kwong FY. Org. Lett. 2007; 9: 3469
- 14c Wang F. Liu H. Fu H. Jiang Y. Zhao Y. Org. Lett. 2009; 11: 2469
- 14d Kálai T. Bognár B. Zsolnai D. Berente Z. Hideg K. Synthesis 2012; 44: 3655
- 14e Malakar CC. Schmidt D. Conrad J. Beifuss U. Org. Lett. 2011; 13: 1972
- 15 Nishibayashi Y. Yoshikawa M. Inada Y. Hidai M. Uemura S. J. Org. Chem. 2004; 69: 3408
- 17 Utermoehlen CM. Singh M. Lehr RE. J. Org. Chem. 1987; 52: 5574
- 18 Zeevaart JG. Parkinsown CJ. de Koning CB. Tetrahedron Lett. 2004; 45: 4261
- 19a Xie R. Ling Y. Fu H. Chem. Commun. 2012; 48: 12210
- 19b Bhunia SK. Polley A. Natarajan R. Jana R. Chem. Eur. J. 2015; 21: 16786
- 20 Xie C. Zhang Y. Huang Z. Xu P. J. Org. Chem. 2007; 72: 5431