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Synlett 2013; 24(18): 2431-2436
DOI: 10.1055/s-0033-1339671
DOI: 10.1055/s-0033-1339671
letter
Isoquinoline N-Oxide Synthesis under Pd-Catalysed C–H Activation/Annulation Processes
Further Information
Publication History
Received: 02 July 2013
Accepted after revision: 03 August 2013
Publication Date:
28 August 2013 (online)
![](https://www.thieme-connect.de/media/synlett/201318/lookinside/thumbnails/10.1055-s-0033-1339671-1.jpg)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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