Chinese Journal of Organic Chemistry >
Palladium-Catalyzed Intramolecular [4+2] Cycloadition Reactions of Aryl-Substituted Diynes
Received date: 2015-05-20
Revised date: 2015-06-23
Online published: 2015-07-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272005).
The nitrogen-containing heterocyclic compounds are important organic molecules which could be widely found in nature. Most of them have biologic activity and become the core skeleton of agrochemicals, pharmaceuticals, dyes and organic functional materials. A practical and efficient domino method for the preparation of diversely fused yne-functionalized benzoisoindole from triynes is developed via palladium-catalyzed [4+2] cycloaddition. All new products were fully characterized by various spectroscopic techniques and high-resolution mass spectrometry. The molecular structure of 2g was confirmed using single-crystal X-ray analyses.
Key words: palladium-catalyzed; synthesis; C-C coupling; benzoisoindole derivatives
Wu Yuqin , Yang Yong , Li Lidong . Palladium-Catalyzed Intramolecular [4+2] Cycloadition Reactions of Aryl-Substituted Diynes[J]. Chinese Journal of Organic Chemistry, 2015 , 35(11) : 2333 -2339 . DOI: 10.6023/cjoc201505032
[1] (a) Berglund, M.; Dalence-Guzman, M. F.; Skogvall, S.; Sterner, O. Bioorg. Med. Chem. 2008, 16, 2513.(b) Funk, O. F.; Kettmann, V.; Drimal, J.; Langer, T. J. Med. Chem. 2004, 47, 2750.(c) Berger, D.; Citarella, R.; Dutia, M.; Greenburger, L.; Hallet, W.; Paul, R.; Powell, D. J. Med. Chem. 1999, 42, 2145.(d) Krysko, A. A.; Chugunov, B. M.; Malovichko, O. L.; Andronati, S. A.; Kabanova, T. A.; Karaseva, T. L.; Kiriyak, A. V. Bioorg. Med. Chem. Lett 2004, 14, 5533.
[2] (a) Kukkola, P. J.; Bilci, N. A.; Ikeler, T. J. Tetrahedron Lett. 1996, 37, 5065.(b) Kukkola, P. J.; Bilci, N. A.; Ikler, T.; Savage, P.; Shetty, S. S.; DelGrande, D.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 2001, 11, 1737.
[3] Shi, Q.; Ornstein, P. L.; Briner, K.; Richardson, T. I.; Arnold, M. B.; Backer, R. T.; Buckmaster, J. L.; Canada, E. J.; Doecke, C. W.; Hertel, L. W.; Honigschmidt, N.; Hsiung, H. M.; Husain, S.; Kuklish, S. L.; Martinelli, M. J.; Mullaney, J. T.; O'Brien, T. P.; Reinhard, M. R.; Rothhaar, R.; Shah, J.; Wu, Z.; Xie, C.; Zgombick, J. M.; Fisher, M. J. Bioorg. Med. Chem. Lett. 2006, 16, 2341.
[4] (a) Barnard, T. M.; Vanier, G. S.; Jr, M. J. C. Org. Proc. Res. Dev. 2006, 10, 1233.(b) Williams, F. J.; Jarvo, E. R. Angew. Chem., Int. Ed. 2011, 50, 4459.(c) Zhu, S.; Cao, J.; Wu, L.; Huang, X. J. Org. Chem. 2012, 77, 10409.(d) Clary, K. N.; Parvez, M.; Back, T. G. J. Org. Chem. 2010, 75, 3751.
[5] (a) Hu, Y. M.; Yu, C. L.; Ren, D.; Hu, Q.; Zhang, L. D.; Cheng, D. Angew. Chem., Int. Ed. 2009, 48, 5448.(b) Hu, Y.; Zhu, T.; Mu, X.; Zhao, Q.; Yu, T.; Wen, L.; Zhang, Y.; Wu, M.; Zhang, H. Tetrahedron 2012, 68, 311.(c) Li, L.; Hu, Q.; Zhou, P.; Xie, H.; Zhang, X.; Zhang, H.; Wang, H.; Hu, Y. Synthesis 2014, 46, 1547.
[6] (a) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.(b) Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J.-C. Chem. Soc. Rev. 2012, 41, 3929.
[7] (a) Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326.(b) Ding, Z. H.; Yoshikai, N. Angew. Chem., Int. Ed. 2012, 51, 4698.(c) Yao, B.; Wang, Q.; Zhu, J. P. Angew. Chem., Int. Ed. 2012, 51, 12311.
[8] (a) Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834.(b) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722.
[9] (a) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D.; Saá, C. Org. Lett. 2000, 2, 1497.(b) Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 1999, 40, 7701.
[10] (a) Kawano, T.; Suehiro, M.; Ueda, I. Chem. Lett. 2006, 35, 58.(b) Kawano, T.; Inai, H.; Miyawaki, K.; Ueda, I. Tetrahedron Lett. 2005, 46, 1233.
[11] (a) Yun, S. Y.; Wang, K.-P.; Kim, M.; Lee, D. J. Am. Chem. Soc. 2012, 134, 10783.(b) Yun, S. Y.; Wang, K.-P.; Kim, M.; Lee, D. J. Am. Chem. Soc. 2010, 132, 8840.
[12] (a) Robinson, J. M.; Sakai, T.; Okano, K.; Kitawaki, T.; Danheiser, R. L. J. Am. Chem. Soc. 2010, 132, 11039.(b) Sakai, T.; Danheiser, R. L. J. Am. Chem. Soc. 2010, 132, 12303.(c) Yu, S. C.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074.(d) Kawano, M.; Kiuchi, T.; Negishi, S.; Tanaka, H.; Hoshikawa, T.; Matsuo, J. I.; Ishibashi, H. Angew. Chem., Int. Ed. 2013, 52, 906.
[13] (a) Zhang, H.; Hu, Q.; Li, L.; Hu, Y.; Zhou, P.; Zhang, X.; Xie, H.; Yin, F.; Hu, Y.; Wang, S. Chem. Commun. 2014, 50, 3335.(b) Wu, Y.; Yu, L.; Zhang, Q.; Li, L. Chin. J. Org. Chem. 2015, 35, 724 (in Chinese). (吴玉芹, 于凉云, 张奇, 李立冬, 有机化学, 2015, 35, 724.)
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