1,3-Dipolar cycloadditions of nonstabilized azomethine ylides to planar chalcones via regio- and stereoselective route: A three-component strategy

References

• (a) Longeon, A.; Guyot, M.; Vacelet, J. J. Experentia 1990, 46, 548–556; (b) Klumpp, D. A.; Yeung, K. Y.; Prakash, G. K. S; Olah, G. A. J. Org. Chem. 1998, 63, 4481–4484; (c) Kobayashi, J.; Touda, M.; Agemi, K.; Shigemori, H.; Ishibashi, M.; Saski, T.; Mikami, Y. Tetrahedron 1991, 47, 6617–6622; (d) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545–8553; (e) James, D. M.; Kunze, H. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1137–1140.
   Google Scholar
• (a) Cooper, R. A.; Huxtable, R. J. Toxicon 1996, 34, 604–607; (b) Yan, C. C.; Huxtable, R. J. Life Sci. 1995, 57, 617–626; (c) Yan, C. C.; Huxtable, R. J. Biochem. Pharmacol. 1996, 51, 375–379 (d) Yan, C. C.; Huxtable, R. J. Proc. West. Pharmacol. Soc. 1995, 38, 37–40.
   PubMed Web of Science ®Google Scholar
• (a) Hartmann, T.; Witte, L. In Alkaloids: Chemical and Biological Perspectives; S. W. Pelletier (Ed.); Pergamon: Oxford, 1995; (b) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: New York, 1986; (c) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497–534.
   Google Scholar
• (a) Grigg, R.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 180–181; (b) Grigg, R.; Aly, M. F.; Shridharan, V.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 182–183; (c) Ardil, H.; Grigg, R.; Shridharan, V.; Surendrakumar, S.; Thianpatanagul, S.; Kanajun, S. J. Chem. Soc., Chem. Commun. 1986, 602–604.
   Google Scholar
• Fishwick, C. W. G.; Foster, R. J.; Carr, R. E. Tetrahedron Lett. 1996, 37, 3915–3918.
   Web of Science ®Google Scholar
• Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett. 1998, 39, 2235–2238.
   Web of Science ®Google Scholar
• (a) Bonne, D.; Dekhane, M.; Zhu, J. P. Angew. Chem. Int. Ed. 2007, 46, 2485; (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040–11041; (c) Dömling, A. Chem. Rev. 2006, 106, 17–89.
   Web of Science ®Google Scholar
• (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, UK, 1990; (b) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223–269; (c) Sarrafi, Y.; Asghari, A.; Hamzehloueian, M.; Alimohammadic, K.; Sadatshahabia, M. J. Braz. Chem. Soc. 2013, 24, 1957–1963; (d) Karlsson, S.; Högberg, H. E. Org. Prep. Proc. Int. 2001, 33, 103–172.
   Google Scholar
• (a) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953–4966; (b) Wang, C. L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613–4616.
   Web of Science ®Google Scholar
• (a) Fisera, L.; Sauter, F.; Frolich, J.; Feng, Y.; Ertl, P.; Mereiter, K. Monatsh Chem. 1994, 125, 909–919; (b) Jayashankaran, J.; Manian, R. D. R. S.; Raghunathan, R. Arkivoc 2005, 11, 32–39; (c) Sridhar, G.; Raghunathan, R. Synth Commun. 2006, 36, 21–29.
   Web of Science ®Google Scholar
• (a) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, Germany, 1970; (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976.
   Google Scholar
• Subhramaniyan, G.; Raghunathan, R. Synth. Commun. 2004, 34, 1825–1830.
   Web of Science ®Google Scholar
• Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765–2810.
   PubMed Web of Science ®Google Scholar
• (a) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew Chem. 2007, 119, 1756–1759; (b) Zhang, Q.; Zhang, Z.; Yan, Z.; Liu, Q.; Wang, T. Org Lett. 2007, 9, 3651–3653; (c) Padasani, R. T.; Padasani, P.; Jain, A.; Arora, K. Indian J. Chem. 2006, 45B, 1204–1209.
   Google Scholar
• Alimohammadi, K.; Sarrafi, Y.; Tajbakhsh, M.; Yeganegi, S.; Hamzehloueian, M. Tetrahedron 2011, 67, 1589–1597.
   Web of Science ®Google Scholar
• Dondas, H. A.; Fishwick, C. W. G; Grigg, R.; Kilnera, C. Tetrahedron 2004, 60, 3473–3485.
   Web of Science ®Google Scholar
• Ning, F.; Anderson, R. J.; Hibbs, D. E.; Groundwater, P. W. Tetrahedron Lett. 2010, 51, 843–845.
   Web of Science ®Google Scholar
• (a) Zarghi, A.; Arefi, H.; Dadrass, O. G.; Torabi, S. Med. Chem. Res. 2010, 19, 782–793; (b) Krizevski, R.; Bar, E.; Shalit, O.; Sitrit, Y.; Ben-Shabat, S.; Lewinsohn, E. Phytochemistry 2010, 71, 895–903; (c) Nakano, H.; Osone, K.; Takeshita, M.; Kwon, E.; Seki, C.; Matsuyama, H.; Takano, N.; Kohari, Y. Chem. Commun. 2010, 46, 4827–4829; (d) Tilford, C. H.; Van Campen, J.; Shelton, R. S. J. Am. Chem. Soc. 1947, 69, 2902–2906.
   Web of Science ®Google Scholar
• Orsini, F.; Pelizzoni, F.; Forte, M.; Destro, R.; Gariboldi, P. Tetrahedron 1988, 44, 519–541.
   Web of Science ®Google Scholar
• Sridhar, G.; Gunasundari, T.; Raghunathan, R. Tetrahedron Lett. 2007, 48, 319–322.
   Web of Science ®Google Scholar
• Oh, K.; Li, J. Y.; Ryu, J. Org. Biomol. Chem. 2010, 8, 3015–3024.
   PubMed Web of Science ®Google Scholar
• (a) Sustmann, R.; Trill, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 838–840; (b) Sustmann, R. Pure Appl. Chem. 1974, 40, 569–593.
   Web of Science ®Google Scholar
• Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc., 1973, 95, 7287–7301.
   Web of Science ®Google Scholar
• Houk, K. N. J. Am. Chem. Soc. 1972, 94, 8953–8955.
   Web of Science ®Google Scholar
• (a) Gayen, B.; Banerji, A. Monatsh. Chem. 2014, 145, 1953–1965; (b) Gayen, B.; Banerji, A. J. Heterocycl. Chem. 2015, 52, 919–925.
   Web of Science ®Google Scholar
• (a) Chattaraj, P. K.; Sarkar, U.; Roy, D. R. Chem. Rev. 2006, 106, 2065–2091; (b) Domingo, L. R.; Aurell, M. J.; Pérez, P.; Contreras, R. Tetrahedron 2002, 58, 4417–4423; (c) Chamorro, E.; Chattaraj, P. K.; Fuentealba, P. J. Phys. Chem. (A) 2003, 107, 7068–7072.
   PubMed Web of Science ®Google Scholar
• Yang, W.; Mortier, W. J. J. Am. Chem. Soc. 1986, 108, 5708–5711.
   PubMed Web of Science ®Google Scholar
• Chandra, A. K.; Nguyen, M. T. J. Chem. Soc. Perkin Trans. 2 1997, 1415–1418.
   Google Scholar
• Stecko, S.; Pasniczek, K.; Michel, C.; Milet, A.; Perez, S.; Chmielewski, M. Tetrahedron: Asymmetry 2008, 19, 1660–1669.
   Web of Science ®Google Scholar
• (a) Das, T. K.; Salampuria, S.; Banerjee, M. J. Mol. Struct.: THEOCHEM 2010, 959, 22–29; (b) Alimohammadi, K.; Sarrafi, Y.; Tajbakhsh, M.; Yeganegi, S.; Hamzehloueian, M. Tetrahedron 2011, 67, 1589–1597.
   Web of Science ®Google Scholar
• Koopmans, T. A. Physica 1933, 1, 104–113.
   Google Scholar
• Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512–7516.
   Web of Science ®Google Scholar
• Acharjee, N.; Banerji, A.; Prange, T. Monatsh. Chem. 2010, 141, 213–221.
   Web of Science ®Google Scholar
• Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066–4073.
   Web of Science ®Google Scholar
• Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, rev. D.01 (Gaussian Inc.: Wallingford, CT, 2004).
   Google Scholar
• Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239–245.
   Web of Science ®Google Scholar
• Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117–129.
   Web of Science ®Google Scholar