LOGIN TO YOUR ACCOUNT

Username
Password
Remember Me
Or use your Academic/Social account:

CREATE AN ACCOUNT

Or use your Academic/Social account:

Congratulations!

You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.

Important!

Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message

CREATE AN ACCOUNT

Name:
Username:
Password:
Verify Password:
E-mail:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
Publisher: American Chemical Society
Languages: English
Types: Article
Subjects:
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.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

    • (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.
  • No related research data.
  • No similar publications.

Share - Bookmark

Cite this article