Efficient 1,6-addition reactions of 3-substituted oxindoles: Access to isoxazole-fused 3,3′-disubstituted oxindole scaffolds and hexahydro-1h-pyrido[2,3-b]indol-2-one scaffolds

References

• (a) Hirano, A.; Iwai, Y.; Masuma, R.; Tei, K.; Omura, S. J. Antibiot. 1979, 32, 781–785; (b) Konda, Y.; Onda, M.; Hirano, A.; Omura, S. Chem. Pharm. Bull. 1980, 28, 2987–2993; (c) Koizumi, Y.; Arai, M.; Tomoda, H.; Omura, S. Biochim. Biophys. Acta Mol. Cell Res. 2004, 1693, 47–55.
   Web of Science ®Google Scholar
• (a) Steyn, P. S. Tetrahedron 1970, 26, 51–57; (b) Nozawa, K.; Nakajima, S. J. Nat. Prod. 1979, 42, 374–377; (c) Kozlovsky, A. G.; Vinokurova, N. G.; Reshetilova, T. A.; Sakharovsky, V. G.; Baskunov, B. P.; Seleznyov, S. G. Appl. Biochem. Microbiol. 1994, 30, 410–414; (d) Overy, D. P.; Phipps, R. K.; Frydenvang, K.; Larsen, T. O. Biochem. Syst. Ecol. 2006, 34, 345–348; (e) Du, L.; Li, D.; Zhu, T.; Cai, S.; Wang, F.; Xiao, X.; Gu, Q.; Tetrahedron 2009, 65, 1033–1039; (f) Du, L.; Feng, T.; Zhao, B.; Li, D.; Cai, S.; Zhu, T.; Wang, F.; Xiao, X.; Gu, Q. J. Antibiot. 2010, 63, 165–170.
   Google Scholar
• (a) Nakao, Y.; Yeung, B. K. S.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. J. Am. Chem. Soc., 1995, 117, 8271–8272; (b) Nakao, Y.; Kuo, J.; Yoshida, W. Y.; Kelly, M.; Scheuer, P. J. Org. Lett., 2003, 5, 1387–1390; (c) Yeung, B. K. S.; Nakao, Y.; Kinnel, R. B.; Carney, J. R.; Yoshida, W. Y.; Scheuer, P. J. J. Org. Chem. 1996, 61, 7168–7173; (d) Luo, S. P.; Peng, Q. L.; Xu, C. P.; Wang, A. E.; Huang, P. Q. Chinese J. Chem. 2014, 32, 757–770; (e) Guo, C.; Song, J.; Luo, S.-W.; Gong, L.-Z. Angew. Chem. Int. Ed. 2010, 49, 5558–5562 (f) He, R.; Ding, C.; Maruoka, K. Angew. Chem. Int. Ed. 2009, 48, 4559–4561.
   Google Scholar
• For selected reviews and highlights on 1,6-addition reactions, see: (a) Csákÿ, A. G.; Herrán, G.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080–4102; (b) Biju, A. T. Chem. Cat. Chem. 2011, 3, 1847–1849; (c) Silva, E. M. P.; Silva, A. M. S. Synthesis 2012, 44, 3109–3128; (d) Lear, M. J.; Hayashi, Y. Chem. Cat. Chem. 2013, 5, 3109–3521; (e) Chauhan, P.; Kaya, U.; Endersa, D. Adv. Synth. Catal. 2017, 359, 888–912.
   Web of Science ®Google Scholar
• As for the 3-methyl-4-nitro-5-alkenyl-isoxazole substrates used in this work, only the E isomers can be obtained according to the procedures reported by Adamo and co-workers. For details, see: (a) Adamo, M. F. A.; Duffy, E. F.; Konda, V. R.; Murphy, F. Heterocycles 2007, 71, 1173–1181; (b) Adamo, M. F. A.; Donati, D.; Duffy, E. F.; Sarti-Fantoni, P. Tetrahedron 2007, 63, 2047–2052.
   Web of Science ®Google Scholar
• For some representative examples relevant to the 1,6-addition Michael addition reactions of 3-methyl-4-nitro-5-alkenyl-isoxazoles with various nucleophiles, see: (a) Baschieri, A.; Bernardi, L.; Ricci, A.; Suresh, S.; Adamo, M. F. A. Angew. Chem., Int. Ed. 2009, 48, 9342–9345; (b) Fini, F.; Nagabelli, M.; Adamo, M. F. A. Adv. Synth. Catal. 2010, 352, 3163–3168; (c) Adamo, M. F. A.; Donati, D.; Duffy, E. F.; Sarti-Fantoni, P. J. Org. Chem. 2005, 70, 8395–8399; (d) Adamo, M. F. A.; Duffy, E. F.; Donati, D.; Sarti-Fantoni, P. Tetrahedron 2007, 63, 2684–2688; (e) Adamo, M. F. A.; Konda, M. R. Org. Lett. 2007, 9, 303–305; (f) Disetti, P.; Moccia, M.; Illera, D. S.; Suresh, S.; Adamo, M. F. A. Org. Biomol. Chem. 2015, 13, 10609–10612.
   Web of Science ®Google Scholar
• Liu, X.-L.; Zhang, W.-H.; Yao, Z.; Liu, X.-W.; Peng, L.-J.; Zhao, Z.; Lu, Y.; Zhou, Y.; Yuan, W.-C. Tetrahedron 2015, 71, 9483–9495.
   Web of Science ®Google Scholar
• (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893–930; (b) Gil, C.; Brase, S. J. Comb. Chem. 2009, 11, 175–197.
   Google Scholar
• For selected reviews, see: (a) Hibino, S.; Choshi, T. Nat. Prod. Rep. 2001, 18, 66–87; (b) Da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273–324; (c) Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 12, 2209–2219; (d) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945–2964; (e) Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36–51; (f) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748–8758.
   PubMed Web of Science ®Google Scholar
• (a) Shangary, S.; Qin, D. G.; McEachern, D.; Liu, M. L.; Miller, R. S.; Qiu, S.; Nikolovska-Coleska, Z.; Ding, K.;Wang, G. P.; Chen, J. Y.. Proc. Natl. Acad. Sci. U. S. A. 2008, 105(10):3933–3938; (b) Luk, K-C.; So, S-S.; Zhang, J.; Zhang, Z. Preparation of Oxindoles as Inhibitors of MDM2-p53 Interaction for the Treatment of Cancer. W02006136606[P].
   PubMed Web of Science ®Google Scholar
• Daidone, G.; Raffa, D.; Maggio, B.; Plescia, F.; Cutuli, V. M. C.; Mangano, N. G.; Caruso, A. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 50–54.
   PubMed Web of Science ®Google Scholar
• Al-Tel, T. H.; Al-Qawasmeh, R. A.; Zaarour, R. Eur. J. Med. Chem., 2011, 46, 1874–1881.
   PubMed Web of Science ®Google Scholar
• Li, W.-T.; Hwang, D.-R.; Chen, C.-P.; Shen, C.-W.; Huang, C.-L.; Chen, T.-W.; Lin, C.-H.; Chang, Y.-L.; Chang, Y.-Y.; Lo, Y.-K.; J. Med. Chem., 2003, 46, 1706–1715.
   PubMed Web of Science ®Google Scholar
• (a) Ratcliffe, P.; Maclean, J.; Abernethy, L.; Clarkson, T.; Dempster, M.; Easson, A.-M.; Edwards, D.; Everett, K.; Feilden, H.; Littlewood, P.; Bioorg. Med. Chem. Lett. 2011, 21, 2559–2563; (b) Roman, B. I.; De Ryck, T.; Dierickx, L.; Vanhoecke, B. W. A.; Katritzky, A. R.; Bracke, M.; Stevens, C. V. Bioorg. Med. Chem. 2012, 20, 4812–4819.
   Web of Science ®Google Scholar
• (a) Cao, Z.-Y.; Wang, Y.-H.; Zeng, X.-P.; Zhou, J. Tetrahedron Letters 2014, 55, 2571–2584; (b) Jiang, K.; Chen, Y.-C. Tetrahedron Letters 2014, 55, 2049–2055; (c) Ziarani, G. M.; Moradi, R.; Lashgari, N. Tetrahedron: Asymmetry 2015, 26, 517–541; (d) Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023–1052; (e) Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev., 2012, 41, 7247–7290; (f) Zhou, F.; Liu, Y. L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381–1407.
   Web of Science ®Google Scholar
• (a) Yang, Y.; Moinodeen, F.; Chin, W.; Ma, T.; Jiang, Z.; Tan, C.-H. Org. Lett. 2012, 14, 4762–4765; (b) Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593–1595.
   Google Scholar