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Publisher: American Chemical Society
Languages: English
Types: Article
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The first Rh-catalyzed C-H amidation of pyridines is reported. The incorporation of a substituent at the C2 position both is crucial to the success of this transformation and provides considerable scope for further elaboration of the resulting products. Among these compounds, 2-chloropyridines allow access to a selection of intermediates including a versatile azaquinazoline scaffold.
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- (1) For representative examples of N-heterocycle synthesis from anthranilic acid derivatives see: a) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469-6480; b) Prajapati, S. M.; Patel, K. D.; Vekariya, R. H.; Panchal, S. N.; Patel, H. D. RSC Adv. 2014, 4, 24463-24476; c) Connolly, D. J.; Cusack, D.; T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153-10202.
- (2) For representative reviews on C-H activation see: a) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094-5115; b) Sarkar, S. D.; Liu, W.; Kozhushkov, I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461-1429; c) Song, G.; Wang, F.; Li, X.; Chem. Soc. Rev. 2012, 41, 3651- 3678; d) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053-1064; e) Lyons, T. W.; Sanford, M. Chem. Rev. 2010, 110, 1147-1169; f) Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814-825. For C-H activation approaches to anthranilic acid derivative synthesis see: a) Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862-12864; b) Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466- 1474; c) Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem. Int. Ed. 2012, 51, 9904-9908; d) Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2013, 15, 3014-3017; e) Kim, J.; Chang, S. Angew. Chem. Int. Ed. 2014, 53, 2203-2207; f) Giri, R; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686-693.
- (4) Maiden, T. M. M., Swanson, S.; Procopiou, P. A.; Harrity, J. P. A. Chem.-Eur. J. 2015, 21, 14342-14346.
- (5) Mei, R.; Loup, J.; Ackermann, L. ACS Catal 2016, 6, 793-797.
- (6) Qin, Q.; Yu, S.; Org. Lett. 2014, 16, 3504-3507.
- (7) Shang, M.; Zeng, S.-H.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. Org. Lett., 2013, 15, 5286-5289.
- (8) Matsubara, T.; Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2014, 136, 646-649.
- (9) For reported C-H amidation upon pyridines see: a) Shang, M.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354-3357; b) Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem. Int. Ed. 2013, 52, 6043-6046; c) Roane, J.; Daugulis, O. J. Am. Chem. Soc. 2016, 138, 4601-46-47.
- (10) For further details see Supporting Information.
- (11) Lafaye, K.; Nicolas, L.; Guérinot, A.; Reymond, S.; Cossy, J. Org. Lett. 2014, 16, 4972-4975.
- (12) Subjecting these substrates to reaction conditions in CD3OD failed to return deuterated substrate, see Supporting Information for details. For the use of related compounds as ligands for transition metal catalysis see: Nishiyama, H.; Yamaguchi, S.; Park, S-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143-150.
- (13) Chang, L.; Lee, S.-Y.; Leonczak, P.; Rozenski, J.; De Jonghe, S.; Hanck, T.; Muller, C. E.; Herdwijn, P. J. Med. Chem. 2014, 57, 10080-10100.
- (14) a) Chai, Y.; Paul, Y.; Rettig, M.; Wilson, W. D.; Boykin, D. W. J. Org. Chem. 2014, 79, 852-866; b) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H.; J. Am. Chem. Soc. 2002, 124, 13856- 13863; c) Petersen, J. G.; Sørensen, T.; Damgaard, M.; Nielsen, B.; Jensen, A. A.; Balle, T.; Bergmann, R.; Frølund, B. Eur. J. Med. Chem. 2014, 84, 404-416.
- (15) Sadler, S. A.; Tajuddin, H.; Mkhalid, I. A. I.; Batsanov, A. S.; Albesa-Jove, D.; Cheung, M. S.; Maxwell, A. C.; Shukla, L.; Roberts, B.; Blakemore, D. C.; Lin, Z.; Marder, T. B.; Steel, P. G.; Org. Biomol. Chem. 2014, 12, 7318-7327.
- (16) Crawford, T. D.; Ndubaku, C. O.; Chen, H.; Boggs, J. W.; Bravo, B. J.; DeLaTorre, K.; Giannetti, A. M.; Gould, S. E.; Harris, S. F.; Magnuson, S. R.; McNamara, E.; Murray, L. J.; Nonomiya, J.; Sambrone, A.; Schmidt, S.; Smyczek, T.; Stanley, M.; Vitorino, P.; Wang, L.; West, K.; Wu, P.; Ye, W. J. Med. Chem. 2014, 57, 3484-3493.
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