Ligand-Enabled Triple CH Activation Reactions: One-Pot Synthesis of Diverse 4-Aryl-2-quinolinones from Propionamides†
Dr. Youqian Deng
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Wei Gong
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
These authors contributed equally to this work.
Search for more papers by this authorJian He
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Quan Yu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)Search for more papers by this authorDr. Youqian Deng
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Wei Gong
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
These authors contributed equally to this work.
Search for more papers by this authorJian He
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Quan Yu
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)Search for more papers by this authorWe gratefully acknowledge The Scripps Research Institute and the NIH (NIGMS, 2R01GM084019) for financial support.
Graphical Abstract
Building complexity: Diverse 4-aryl-2-quinolinones such as 1 are prepared from propionamides in one pot by pyridine ligand-promoted triple sequential CH activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new CC bonds and one CN bond are formed to rapidly build molecular complexity from propionic acid.
Abstract
Diverse 4-aryl-2-quinolinones are prepared from propionamides in one pot by ligand-promoted triple sequential CH activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new CC bonds and one CN bond are formed to rapidly build molecular complexity from propionic acid.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie_201403878_sm_miscellaneous_information.pdf2.1 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1K. S. L. Chan, M. Wasa, L. Chu, B. N. Laforteza, M. Miura, J.-Q. Yu, Nat. Chem. 2014, 6, 146.
- 2
- 2aJ. He, S. Li, Y. Deng, H. Fu, B. N. Laforteza, J. E. Spangler, A. Homs, J.-Q. Yu, Science 2014, 343, 1216;
- 2bM. Wasa, K. S. L. Chan, X.-G. Zhang, J. He, M. Miura, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 18570.
- 3
- 3aJ. He, M. Wasa, K. S. L. Chan, J.-Q. Yu, J. Am. Chem. Soc. 2013, 135, 3387;
- 3bM. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 9886.
- 4
- 4a Catalytic Cascade Reactions (Eds.: ), Wiley-VCH, Weinheim, 2013; for selected examples of cascade reactions involving palladium-catalyzed CH activations, see:
- 4bG.-W. Wang, T.-T. Yuan, D.-D. Li, Angew. Chem. 2011, 123, 1416; Angew. Chem. Int. Ed. 2011, 50, 1380;
- 4cJ. Karthikeyan, C.-H. Cheng, Angew. Chem. 2011, 123, 10054;
10.1002/ange.201104311 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 9880;
- 4dT. Piou, L. Neuville, J. Zhu, Angew. Chem. 2012, 124, 11729;
10.1002/ange.201206267 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 11561;
- 4eT. Piou, A. Bunescu, Q. Wang, L. Neuville, J. Zhu, Angew. Chem. 2013, 125, 12611;
10.1002/ange.201306532 Google ScholarAngew. Chem. Int. Ed. 2013, 52, 12385;
- 4fT. Piou, L. Neuville, J. Zhu, Org. Lett. 2012, 14, 3760.
- 5For natural products, see:
- 5aY. Kitahara, M. Shimizu, A. Kubo, Heterocycles 1990, 31, 2085;
- 5bY. Kobayashi, T. Harayama, Org. Lett. 2009, 11, 1063, and references therein.
- 6For selected important medicinal products, see:
- 6aP. R. Angibaud, M. G. Venet, W. Filliers, R. Broeckx, Y. A. Ligny, P. Muller, V. S. Poncelet, D. W. End, Eur. J. Org. Chem. 2004, 479;
- 6bB. M. Andresen, M. Couturier, B. Cronin, M. D’Occhio, M. D. Ewing, M. Guinn, J. M. Hawkins, V. J. Jasys, S. D. LaGreca, J. P. Lyssikatos, G. Moraski, K. Ng, J. W. Raggon, A. M. Stewart, D. L. Tickner, J. L. Tucker, F. J. Urban, E. Vazquez, L. Wei, Org. Process Res. Dev. 2004, 8, 643;
- 6cE. van Cutsem, H. van de Velde, P. Karasek, H. Oettle, W. L. Vervenne, A. Szawlowski, P. Schoffski, S. Post, C. Verslype, H. Neumann, H. Safran, Y. Humblet, J. P. Ruixo, Y. Ma, D. von Hoff, J. Clin. Oncol. 2004, 22, 1430;
- 6dP. Cheng, Q. Zhang, Y.-B. Ma, Z.-Y. Jiang, X.-M. Zhang, F.-X. Zhang, J.-J. Chen, Bioorg. Med. Chem. Lett. 2008, 18, 3787;
- 6eM.-H. Chen, P. Fitzgerald, S. B. Singh, E. A. O’Neill, C. D. Schwartz, C. M. Thompson, S. J. O’Keefe, D. M. Zallerb, J. B. Doherty, Bioorg. Med. Chem. Lett. 2008, 18, 2222;
- 6fM. J. Wall, J. Chen, S. Meegalla, S. K. Ballentine, K. J. Wilson, R. L. DesJarlais, C. Schubert, M. A. Chaikin, C. Crysler, I. P. Petrounia, R. R. Donatelli, E. J. Yurkow, L. Boczon, M. Mazzulla, M. R. Player, R. J. Patch, C. L. Manthey, C. Molloy, B. Tomczuk, C. R. Illig, Bioorg. Med. Chem. Lett. 2008, 18, 2097;
- 6gJ. M. Kraus, C. L. M. J. Verlinde, M. Karimi, G. I. Lepesheva, M. H. Gelb, F. S. Buckner, J. Med. Chem. 2009, 52, 1639;
- 6hJ. M. Kraus, H. B. Tatipaka, S. A. McGuffin, N. K. Chennamaneni, M. Karimi, J. Arif, C. L. M. J. Verlinde, F. S. Buckner, M. H. Gelb, J. Med. Chem. 2010, 53, 3887.
- 7For selected examples of synthesis of 4-aryl-2-quinolinones, see:
- 7aJ. Ferguson, F. Zeng, N. Alwis, H. Alper, Org. Lett. 2013, 15, 1998;
- 7bK. Inamoto, J. Kawasaki, K. Hiroya, Y. Kondo, T. Doi, Chem. Commun. 2012, 48, 4332;
- 7cR. Berrino, S. Cacchi, G. Fabrizi, A. Goggiamani, J. Org. Chem. 2012, 77, 2537;
- 7dT. Shibuya, Y. Shibata, K. Noguchi, K. Tanaka, Angew. Chem. 2011, 123, 4049;
10.1002/ange.201100152 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 3963;
- 7eK. Inamoto, T. Saito, K. Hiroya, T. Doi, J. Org. Chem. 2010, 75, 3900;
- 7fM. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14058;
- 7gG. Battistuzzi, R. Bernini, S. Cacchi, I. De Salve, G. Fabrizi, Adv. Synth. Catal. 2007, 349, 297;
- 7hN. A. Cortese, C. B. Ziegler, Jr., B. J. Hrnjez, R. F. Heck, J. Org. Chem. 1978, 43, 2952.
- 8The N-deprotection of product 3 x derived from 2,6-difluoro-4-methoxyaniline was also extensively tried under different conditions, but has not been realized so far.
- 9A. Nakazaki, A. Mori, S. Kobayashi, T. Nishikawa, Tetrahedron Lett. 2012, 53, 7131.
- 10K. Hino, K. Furukawa, Y. Nagai, H. Uno, Chem. Pharm. Bull. 1980, 28, 2618.
- 11R. Labaudinière, W. Hendel, B. Terlain, F. Cavy, O. Marquis, N. Dereu, J. Med. Chem. 1992, 35, 4306.
- 12R. Bernini, S. Cacchi, I. D. Salve, G. Fabrizi, Synlett 2006, 2947.
- 13For selected examples involving palladium-catalyzed dehydrogenations, see:
- 13aW. Gao, Z. He, Y. Qian, J. Zhao, Y. Huang, Chem. Sci. 2012, 3, 883;
- 13bT. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566;
- 13cT. Diao, T. J. Wadzinski, S. S. Stahl, Chem. Sci. 2012, 3, 887;
- 13dT. Diao, D. Pun, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 8205;
- 13eZ. Huang, G. Dong, J. Am. Chem. Soc. 2013, 135, 17747;
- 13fN. Gigant, J.-E. Bäckvall, Chem. Eur. J. 2014, 20, 5890.
- 14M.-L. Louillat, F. W. Patureau, Chem. Soc. Rev. 2014, 43, 901.
