A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides

References

• For reviews on the [3 + 2]-cycloaddition chemistry of azomethine ylides, see: (a) Kanemasa, S. Heterocycles. 2010, 82, 87. DOI: 10.3987/REV-10-666. (b) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484–4517. DOI: 10.1021/cr050011g. (c) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765–2810. DOI: 10.1021/cr040004c. (d) Husinec, S.; Savic, V. V. Tetrahedron: Asymmetry. 2005, 16, 2047–2061. DOI: 10.1016/j.tetasy.2005.05.020. (e) Najera, C.; Sansano, J. M. Coc. 2003, 7, 1105–1150. DOI: 10.2174/1385272033486594.
   Web of Science ®Google Scholar
  (f) Padwa, A.; Pearson, W. H., Eds. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Wiley: New York, 2002.
   Google Scholar
  (g) Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 232.
   Google Scholar
• For reviews on 1,5- and 1,7-electrocyclizations of conjugated 1,3-dipoles, see: (a) Nyerges, M.; Tóth, J.; Groundwater, P. W. Synlett. 2008, 2008, 1269–1278. DOI: 10.1055/s-2008-1072743. (b) Pinho e Melo, T. M. V. D. Eur. J. Org. Chem. 2006, 2873.  (c) Groundwater, P. W.; Nyerges, M. Adv. Heterocycl. Chem. 1999, 73, 97. DOI: 10.1002/ejoc.200500892. (d) Zecchi, G. Synthesis. 1991, 1991, 181–188. DOI: 10.1055/s-1991-26413. (e) Huisgen, R. Angew. Chem. Int. Ed. Engl. 1980, 19, 947–973. DOI: 10.1002/anie.198009473. (f) Taylor, E. C.; Turchi, I. J. Chem. Rev. 1979, 79-96., DOI: 10.1002/anie.198009473.
   Web of Science ®Google Scholar
• (a) Seidel, D. Acc. Chem. Res. 2015, 48, 317–328. DOI: 10.1021/ar5003768.
   PubMed Web of Science ®Google Scholar
  (b) Zhang, C.; Das, D.; Seidel, D. Chem. Sci. 2011, 2, 233–236. DOI: 10.1039/C0SC00432D.
   Web of Science ®Google Scholar
• (a) Hartung, J.; Greszler, S. N.; Klix, R. C.; Kallemeyn, J. M. Org. Process. Res. Dev. 2019, 23, 2532–2537. DOI: 10.1021/acs.oprd.9b00292.
   Web of Science ®Google Scholar
  (b) Zhao, Y.; Yu, S.; Sun, W.; Liu, L.; Lu, J.; McEachern, D.; Shargary, S.; Bernard, D.; Li, X.; Zhao, T.; et al. J. Med. Chem. 2013, 56, 5553–5561. DOI: 10.1021/jm4005708.
   PubMed Web of Science ®Google Scholar
  (c) Efremov, I. V.; Vajdos, F. F.; Borzilleri, K. A.; Capetta, S.; Chen, H.; Dorff, P. H.; Dutra, J. K.; Goldstein, S. W.; Mansour, M.; McColl, A.; et al. J. Med. Chem. 2012, 55, 9069–9088. DOI: 10.1021/jm201715d.
   PubMed Web of Science ®Google Scholar
  (d) Zhan, Y.; Liu, T.; Ren, J.; Wang, Z. Chemistry. 2017, 23, 17862–17866. DOI: 10.1002/chem.201704695.
   PubMed Web of Science ®Google Scholar
  (e) Fang, X.; Wang, C. J. Org. Biomol. Chem. 2018, 16, 2591–2601. DOI: 10.1039/C7OB02686B.
   PubMed Web of Science ®Google Scholar
  (f) Wang, Y. M.; Zhang, H. H.; Li, C.; Fan, T.; Shi, F. Chem. Commun. (Camb.) 2016, 52, 1804–1807. DOI: 10.1039/c5cc07924a.
   PubMed Web of Science ®Google Scholar
• (a) Santos, M. M. M. Tetrahedron. 2014, 70, 9735–9757. DOI: 10.1016/j.tet.2014.08.005.
   Web of Science ®Google Scholar
  (b) Dai, W.; Jiang, X. L.; Wu, Q.; Shi, F.; Tu, S. J. J. Org. Chem. 2015, 80, 5737–5744. DOI: 10.1021/acs.joc.5b00708.
   PubMed Web of Science ®Google Scholar
  (c) Wang, C. S.; Zhu, R. Y.; Zheng, J.; Shi, F.; Tu, S. J. J. Org. Chem. 2015, 80, 512–520. DOI: 10.1021/jo502516e.
   PubMed Web of Science ®Google Scholar
• (a) Bende, Z´n.; Simon, K´l´n.; Tóth, G´b.; Töke, Ĺ.; Weber, L. Liebigs Ann. Chem. 1982, 1982, 924–929. DOI: 10.1002/jlac.198219820512.
   Google Scholar
  (b) Bende, Z. N.; Bitter, I. N.; Toke, L.; Weber, L.; Tóth, G.; Janke, F. Liebigs Ann. Chem. 1982, 1982, 2146–2152. DOI: 10.1002/jlac.198219821205.
   Google Scholar
  (c) Bende, Z.; Töke, L.; Weber, L.; Tóth, G.; Janke, F.; Csonka, G. Tetrahedron. 1984, 40, 369–375. DOI: 10.1016/S0040-4020(01)91183-4.
   Web of Science ®Google Scholar
  (d) Tóth, G.; Tischer, T.; Bende, Z.; Szejtli, G.; Tőke, L. Monatsh. Chem. 1990, 121, 529–537. DOI: 10.1007/BF00810862. .
   Web of Science ®Google Scholar
  (e) Tischer, T.; Tőke, L.; Tóth, G. Acta Chim. Hung 1990, 127, 171.
   Google Scholar
  (f) Janke, F.; Himmelreich, U.; Tóth, G.; Tischer, T.; Kádas, I.; Bende, Z.; Töke, L. J. Het. Chem 1991, 28, 867–873. DOI: 10.1002/jhet.5570280406.
   Web of Science ®Google Scholar
  (g) Fejes, I.; Nyerges, M.; Szöllõsy, Á.; Blaskó, G.; Tõke, L. Tetrahedron. 2001, 57, 1129–1137. DOI: 10.1016/S0040-4020(00)01085-1.
   Web of Science ®Google Scholar
  (h) Nyerges, M.; Somfai, B.; Tóth, J.; Dancsó, A.; Blaskó, G.; Tőke, L. Synthesis. 2005, 2005, 2039–2045. DOI: 10.1055/s-2005-869908.
   Web of Science ®Google Scholar
• Fejes, I.; Nyerges, M.; Tőke, L.; Pak, C. S. Tetrahedron. 2000, 56, 639–644. DOI: 10.1016/S0040-4020(99)01028-5.
   Web of Science ®Google Scholar
• Tóth, J.; Dancsó, A.; Blaskó, G.; Tőke, L.; Groundwater, P. W.; Nyerges, M. Tetrahedron. 2006, 62, 5725–5735. DOI: 10.1016/j.tet.2006.03.088.
   Web of Science ®Google Scholar
• Liu, T. L.; Xue, Z. Y.; Tao, H. Y.; Wang, C. J. Org. Biomol. Chem. 2011, 9, 1980–1986. DOI: 10.1039/c0ob00943a.
   PubMed Web of Science ®Google Scholar
• (a) Trost, B. M.; Zhang, Y. Chemistry. 2011, 17, 2916–2922. DOI: 10.1002/chem.201002569.
   PubMed Web of Science ®Google Scholar
  (b) Furuta, K.; Mizuno, Y.; Maeda, M.; Koyama, H.; Hirata, Y. Chem. Pharm. Bull. 2017, 65, 1093–1097. DOI: 10.1248/cpb.c17-00627.
   PubMed Web of Science ®Google Scholar
  (c) Lathourakis, G. E.; Litinas, K. E. J. Chem. Soc, Perkin Trans. 1 1996, 1, 491. DOI: 10.1039/P19960000491;
   Google Scholar
  (d) Walker, G. N.; Smith, R. T.; Weaver, B. N. J. Med. Chem. 1965, 8, 626–637.
   Web of Science ®Google Scholar
  (c) Corsico, C. A.; Gamba, I. A.; Righetti, P. P.; Tacconi, G.; Gatti, G. J. Chem. Soc, Perkin Trans. 1984, 2, 615–619. DOI: 10.1039/p29840000615.
   Google Scholar
  (d) Yun, Y. K.; Labadie, J. GIT Labor. Fachz. 2000, 44, 1456–1458.
   Google Scholar
  (e) Hu, Y.; Kang, H.; Zeng, B.-W.; Wei, P.; Huang, H. J. Chem. Res. (S) 2008, 2008, 642–643. DOI: 10.3184/030823408X374242.
   Web of Science ®Google Scholar
  (f) Zhang, W.; Go, M.-L. Bioorg. Med. Chem. 2009, 17, 2077–2090. DOI: 10.1016/j.bmc.2008.12.052.
   PubMed Web of Science ®Google Scholar
  (g) Gholamzadeh, P.; Ziarani, G. M.; Badiei, A.; Bahrami, Z. Eur. J. Chem. 2012, 3, 279–282. DOI: 10.5155/eurjchem.3.3.279-282.630.
   Google Scholar
  (h) Daisley, R. W.; Walker, J. J. Chem. Soc. B. 1969, 0, 146–148. DOI: 10.1039/J29690000146.
   Web of Science ®Google Scholar
  (i) Zhou, F.; Zheng, J.; Dong, X.; Zhang, Z.; Zhao, L.; Sha, X.; Li, L.; Wen, R. Loc. 2007, 4, 601–605. DOI: 10.2174/157017807782795484. (j) Xiang, C.; Wu, D.; Wang, L.; Wu, H.; Lu, B.; Zhang, Z.; Li, Y.; Liu, Y.; Zhu, R.; Jin, Y. J. Chem. Pharm. Res. 2014, 6, 307–312;(k) Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. J. Med. Chem. 1998, 41, 2588–2603. DOI: 10.1021/jm980123i. (l) Vieth, M.; Cummins, D. J. J. Med. Chem. 2000, 43, 3020–3032. DOI: 10.1021/jm990609e.
   Web of Science ®Google Scholar
• (a) Palmisano, G.; Lesma, G.; Nali, M.; Rindone, B.; Tollari, S. Synthesis. 1985, 1985, 1072–1074. DOI: 10.1055/s-1985-31434.
   Google Scholar
  (b) Shono, T.; Hamaguchi, H.; Sasaki, M.; Fujita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621–1628. DOI: 10.1021/jo00158a010.
   Web of Science ®Google Scholar
  (c) Kadas, I.; Szanto, G.; Tőke, L.; Simon, A.; Tóth, G. J. Het. Chem. 2007, 44, 1373–1381. DOI: 10.1002/jhet.5570440621.
   Web of Science ®Google Scholar