Synlett, Inhaltsverzeichnis

Synlett 2013; 24(18): 2431-2436
DOI: 10.1055/s-0033-1339671

letter

© Georg Thieme Verlag Stuttgart · New York

Isoquinoline N-Oxide Synthesis under Pd-Catalysed C–H Activation/Annulation Processes

Bingyao Li

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: jhuang@tju.edu.cn

^bSynergetic Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, P. R. of China

,

Pingxuan Jiao

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: jhuang@tju.edu.cn

,

Hongban Zhong

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: jhuang@tju.edu.cn

,

Jianhui Huang*

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: jhuang@tju.edu.cn

^bSynergetic Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, P. R. of China

› Institutsangaben

Alle Artikel dieser Rubrik

Abstract

An oxime directed C–H activation–annulation reaction for the selective synthesis of a range of isoquinoline N-oxides has been developed. Under palladium-catalyzed acid-assisted conditions, the reaction undergoes concerted metallation deprotonation followed by carbopalladation and transmetallation to give polysubstituted isoquinoline N-oxides in moderate to good yields.

Key words

Key words

oxime C–H activation–annulation - isoquinoline N-oxide - palladium catalysis

References

For selected examples, see:

1a Wang L, Huang J, Peng S, Liu H, Jiang X, Wang J. Angew. Chem. Int. Ed. 2013; 52: 1768
1b Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 2084
1c Wang Z.-Q, Liang Y, Lei Y, Zhou M.-B, Li J.-H. Chem. Commun. 2009; 5242
1d Elakkar E, Floris B, Galloni P, Tagliatesta P. Eur. J. Org. Chem. 2005; 889

For selected examples, see:

2a Zhu C, Falck JR. Org. Lett. 2011; 13: 1214
2b McAtee DM. S, Dasgupta S, Watson MP. Org. Lett. 2011; 13: 3490
2c Li DD, Yuan TT, Wang GW. Chem. Commun. 2011; 47: 12789
2d Wang F, Song GY, Li XW. Org. Lett. 2010; 12: 5430

For selected examples, see:

3a Ackermann L, Lygin AV. Org. Lett. 2012; 14: 764
3b Porcheddu A, Mura MG, Luca LD, Pizzetti M, Taddei M. Org. Lett. 2012; 14: 6112
3c Huestis MP, Chan L, Stuart DR, Fagnou K. Angew. Chem. Int. Ed. 2011; 123: 1374
3d Chen JL, Pang QY, Sun YB, Li XW. J. Org. Chem. 2011; 76: 3523
3e Wei XH, Zhao M, Du ZY, Li XW. Org. Lett. 2011; 13: 4636
3f Zhou F, Han XL, Lu XY. Tetrahedron Lett. 2011; 52: 4681
3g Chen JL, Song GY, Pan CL, Li XW. Org. Lett. 2010; 12: 5426
3h Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
3i Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N. Angew. Chem. Int. Ed. 2009; 48: 4572

For selected examples, see:

4a Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142
4b Lu S, Lin Y, Zhong H, Zhao K, Huang J. Tetrahedron Lett. 2013; 54: 2001
4c Zhang N, Li B, Zhong H, Huang J. Org. Biomol. Chem. 2012; 10: 9429
4d Zhong H, Yang D, Wang S, Huang J. Chem. Commun. 2012; 48: 3236
4e Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14952
4f Ackermann L, Lygin AV, Hofmann N. Angew. Chem. Int. Ed. 2011; 50: 6379
4g Song GY, Chen D, Pan CL, Crabtree RH, Li XW. J. Org. Chem. 2010; 75: 7487
4h Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
4i Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010; 39: 744

For selected examples, see:

5a Shi XY, Li CJ. Adv. Synth. Catal. 2012; 354: 2933
5b Ackermann L, Pospech J. Org. Lett. 2011; 13: 4153
5c Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362

For selected examples, see:

6a Kuram MR, Bhanuchandra M, Sahoo AK. Angew. Chem. Int. Ed. 2013; 52: 4607
6b Lee DH, Kwon KH, Yi CS. J. Am. Chem. Soc. 2012; 134: 7325
6c Kundu D, Samim M, Majee A, Hajra A. Chem. Asian J. 2011; 6: 406

For selected examples, see:

7a Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142
7b Ackermann L, Pospech J, Graczyk K, Rauch K. Org. Lett. 2012; 14: 930
7c Chinnagolla RK, Jeganmohan M. Chem. Commun. 2012; 48: 2030
7d Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362
7e Ueura K, Satoh T, Miura M. Org. Lett. 2007; 9: 1470

8a Yu WY, Sit WN, Zhou Z, Chan AS.-C. Org. Lett. 2009; 11: 3174
8b Thirunavukkarasu VS, Parthasarathy K, Cheng C.-H. Angew. Chem. Int. Ed. 2008; 120: 9604

9a Zhang XP, Chen D, Zhao M, Zhao J, Jia AQ, Li XW. Adv. Synth. Catal. 2011; 353: 719
9b Parthasarathy K, Cheng CH. J. Org. Chem. 2009; 74: 9359

10a Chinnagolla RK, Pimparkar S, Jeganmohan M. Org. Lett. 2012; 14: 3032
10b Kornhaaß C, Li J, Ackermann L. J. Org. Chem. 2012; 77: 9190

11 Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
12 Shih WC, Teng CC, Parthasarathy K, Cheng CH. Chem. Asian J. 2012; 7: 306

Zusatzmaterial

Supporting Information