Molecular hybridization-guided annulation reactions of isatins with 4-methylpent-3-en-2-one: A direct access to spirooxindole tetrahydropyranones

References

• (a) Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem. Int. Ed. 1999, 38, 2398–2400; (b) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793–3798; (c) Anada, M.; Washio, T.; Shimada, N.; Kitagaki, S.; Nakajima, M.; Shiro, M.; Hashimoto, S. Angew. Chem. Int. Ed. 2004, 43, 2665–2668; (d) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336–1337; (e) Rajaram, S.; Sigman, M. S. Org. Lett. 2005, 7, 5473–5475; (f) Momiyama, N.; Tabuse, H.; Terada, M. J. Am. Chem. Soc. 2009, 131, 12882–12883 (g) Guin, J.; Rabalakos, C.; List, B. Angew. Chem. Int. Ed. 2012, 51, 8859–8863.
   PubMed Web of Science ®Google Scholar
• (a) Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104–6155; (b) Ball-Jones, N.; Basillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10, 5165–5181.
   PubMed Web of Science ®Google Scholar
• Cui, H.-L.; Tanaka, F. Chem Eur J. 2013, 19, 6213–6216.
   Google Scholar
• Xie, X.; Peng, C.; He, G.; Leng, H.-J.; Wang, B.; Huang, W.; Han, B. Chem. Commun. 2012, 48, 10487–10489.
   PubMed Web of Science ®Google Scholar
• Kandimalla, S. R.; Sabitha, G. Adv. Synth. Catal. 2017, 359, 3444–3453.
   Web of Science ®Google Scholar
• (a) Sun, Z.; Tian, S.; Li, S.; Liu, Y.; Zhang, Y.; Li, Y. Tetrahedron Letters 2017, 58, 3401–3405; (b) Lian, Z.; Shi, M. Eur. J. Org. Chem. 2012, 581–586; (c) Cui, H. L.; Tanaka, F. Chem. Eur. J. 2013, 19, 6213–6216; (d) Cui, H. L.; Chouthaiwale, P. V.; Yin, F.; Tanaka, F. Asian J. Org. Chem. 2016, 5, 153–161; (e) Cui, H. L.; Chouthaiwale, P. V.; Yin, F.; Tanaka, F. Org. Biomol. Chem. 2016, 14, 1777–1783.
   Web of Science ®Google Scholar
• (a) Patra, J. K.; Kim, S. H.; Baek, K. H. J. Food Biochem. 2015, 39(1), 80–90; (b) Li, R.; Hu, H. B.; Li, X. F.; Zhang, P.; Xu, Y. K.; Yang, J. J.; Wang, Y.-F. Food Control 2015, 51, 9–14; (c) Formisano, C.; Oliviero, F.; Rigano, D.; Saab, A. M.; Senatore, F. Ind. Crops Prod. 2014, 62, 405–411; (d) Tian, J.; Zeng, X.; Zhang, S.; Wang, Y.; Zhang, P.; Lu, A.; Peng, X. Ind. Crops Prod. 2014, 59, 69–79; (e) Melgarejo, P.; Calin-Sanchez, A.; Carbonell-Barrachina, A. A.; Martinez-Nicolas, J. J.; Legua, P.; Martinez, R.; Hernandez, F. J. Sci. Food Agric. 2014, 94, 85–94; (f) Liu, P.; Liu, X. C.; Dong, H. W.; Liu, Z. L.; Du, S. S.; Deng, Z. W. Molecules 2012, 17, 14870–14881; (g) Muanda N. F.; Dicko, A.; Soulimani, R. J. Nat. Prod. 2010, 3, 147–160; (h) Riccobono, L.; Maggio, A.; Rosselli, S.; Ilardi, V.; Senatore, F.; Bruno, M. Nat. Prod. Res. 2016, 30, 25–34; (i) Ali, A.; Tabanca, N.; Demirci, B.; Blythe, E. K.; Ali, Z.; Baser, K. H. C.; Khan, I. A. J. Agric. Food Chem. 2015, 63, 447–456.
   Web of Science ®Google Scholar
• Xing, G. X.; Li, N.; Wang, T.; Yao, M. Y. China J. Chin. Mater. Med. 2003, 28, 593–597.
   Google Scholar
• (a) Fukai, T.; Satoh, K.; Nomura, T.; Sakagami, H. Fitoterapia 2003, 74, 720–724; (b) Shi, Y. Q.; Fukai, T.; Sakagami, H.; Chang, W. J.; Yang, P. Q.; Wang, F. P.; Nomura, T. J. Nat. Prod. 2001, 64, 181–188; (c) Tseng, T. H.; Chuang, S. K.; Hu, C. C.; Chang, C. F.; Huang, Y. C.; Lin, C. W.; Lee, Y. J. Tetrahedron 2010, 66, 1335–1340.
   PubMed Web of Science ®Google Scholar
• Zhou, J. J.; Xie, G. R.; Yan, X. J. (Editor). Chemical Composition of Primary Chinese Herb; Science Press: Beijing, 2009; Vol. 1–33.
   Google Scholar
• (a) Calixto, J. B.; Otuki, M. F.; Santos, A. R. S. Planta Med. 2003, 69, 973–983; (b) Rupe, H.; Gassmann, A. Helv. Chim. Acta. 1936, 19, 569; (c) Ferreira, L. A. F.; Henriques, O. B.; Andreoni, A. A. S.; Vital, G. R. F.; Campos, M. M. C.; Habermehl, G. G.; De Moraes, V. L. G.; Toxicon 1992, 30, 1211–1218; (d) Hong, C. H.; Noh, M. S.; Lee, W. Y.; Lee, S. K. Planta Med. 2002, 68, 545–547; (e) Ji, M.; Choi, J.; Lee, J.; Lee, Y. Int. J. Mol. Med. 2004, 14, 253–256; (f) Motoyoshiya, J.; Miyajima, M.; Hirakawa, K.; Kakurai, T. J. Org. Chem. 1985, 50, 1326–1327.
   PubMed Web of Science ®Google Scholar
• Mohamad, K.; Martin, M.-T.; Litaudon, M.; Gaspard, C.; Sévenet, T.; Païs, M. Phytochemistry 1999, 52, 1461–1468.
   Web of Science ®Google Scholar
• Editorial Board of State Administration of Traditional Chinese Medicine: The Chinese Material Medica; Shanghai Science and Technology Press: Shanghai, 1999; Vol. 1–30.
   Google Scholar
• Yang, Q.-Y.; Fang, W.-S. Nat. Prod. Res. Dev. 2003, 15, 66–70.
   Google Scholar
• (a) Jayasinghe, L.; Mallika Kumarihamy, B. M.; Nishantha Jayarathna, K. H. R.; Gayathri Udishani, N. W. M.; Ratnayake Bandara, B. M.; Hara, N.; Fujimoto, Y. Phytochemistry 2003, 62, 637–641; (b) Ohshiro, M.; Kuroyanagi, M.; Ueno, A.; Phytochemistry 1990, 29, 2201–2205; (c) Tuchinda, P.; Saiai, A.; Pohmakotr, M.; Yoosook, C.; Kasisit, J.; Napaswat, C.; Santisuk, T.; Reutrakul, V. Planta Med. 2004, 70, 366–370; (d) Matsuda, H.; Morikawa, T.; Toguchida, I.; Ninomiya, K.; Yoshikawa, M. Chem. Pharm. Bull. 2001, 49, 1558–1566 (e) Yang, Q. Y.; Fang, W. S. Nat. Prod. Res. Dev. 2003, 15, 66–70; (f) Luo, X. D.; Wu, S. H.; Ma, Y. B.; Wu, D. G. Phytochemistry 2000, 54, 801–805; (g) Soares, P. M. G.; Assreuy, A. M. S.; Souza, E. P.; Lima, R. F.; Silva, T. O.; Fontenele, S. R.; Criddle, D. N. Planta Med. 2005, 71, 214–218.
   PubMed Web of Science ®Google Scholar
• CCDC 1578236 Contains The Supplementary Crystallographic Datas for this Paper. These Data can be Obtained Free of Charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
   Google Scholar