SbCl₃-catalyzed solvent-free Friedel–Crafts reaction of phenols with mandelic acids to 3-aryl benzofuran-2(3H)-ones: Synthesis of spirocyclic 2,3-dihydrobenzofuran-2-ones

References

• For recent references on benzofuran-2-ones, see (a) Wang, H.; Dong, B.; Wang, Y.; Li, J.; Shi, Y. Org. Lett. 2014, 16, 186; (b) Li, Y.; Lampkins, A. J.; Baker, M. B.; Sumpter, B. G.; Huang, J.; Abboud, K. A.; Castellano, R. K. Org. Lett. 2009, 11, 4314; (c) Panisheva, E. K.; Alekseeva, L. M.; Evstratova, M. I.; Kiselev, S. S.; Granik, V. G. Pharm. Chem. J. 2007, 41, 549; (d) Kwon, Y.-J.; Sohn, M.-J.; Zheng, C.-J.; Kim, W.-G. Org. Lett. 2007, 9, 2449; (e) Adediran, S. A.; Cabaret, D.; Drouillat, B.; Pratt, R. F.; Wakselman, M. Bioorg. Med. Chem. 2001, 9, 1175; (f) Su, B.-N.; Takaishi, Y.; Tori, M.; Takaoka, S.; Honda, G.; Itoh, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O. Org. Lett. 2000, 2, 493; (g) Close, A.; Haefliger, W.; Hauser, D.; Gubler, H. U.; Dewald, B.; Baggiolini, M. J. Med. Chem. 1981, 24, 1465.
   PubMed Web of Science ®Google Scholar
• (a) Lavielle, G.; Lepagnol, J. US Pat. 4 859 700, 1989; Chem. Abstr. 1989, 110, 75296; (b) Weston, A. W.; Brownell, W. B. J. Am. Chem. Soc. 1952, 74, 653.
   Google Scholar
• For recent references on 3,3-disubstituted benzofuran-2-ones, see (a) Ohmatsu, K.; Ito, M.; Kunieda, T.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 590; (b) Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236; (c) Li, X.; Zhang, Y.-Y.; Xue, X.-S.; Jin, J.-L.; Tan, B.-X.; Liu, C.; Dong, N.; Cheng, J.-P. Eur. J. Org. Chem. 2012, 1774; (d) Wang, D.; Yang, Y.-L.; Jiang, J.-J.; Shi, M. Org. Biomol. Chem. 2012, 10, 7158; (e) Li, X.; Xue, X.-S.; Liu, C.; Wang, B.; Tan, B.-X.; Jin, J.-L.; Zhang, Y.-Y.; Dong, N.; Cheng, J.-P. Org. Biomol. Chem. 2012, 10, 413; (f) Chen, L.; Zhou, F.; Shi, T.-D.; Zhou, J. J. Org. Chem. 2012, 77, 4354; (g) Zhu, C.-L.; Zhang, F.-G.; Meng, W.; Nie, J.; Cahard, D.; Ma, J.-A. Angew. Chem., Int. Ed. 2011, 50, 5869; (h) Pesciaioli, F.; Tian, X.; Bencivenni, G.; Bartoli, G.; Melchiorre, P. Synlett 2010, 1704; (i) Li, X.; Xi, Z.; Luo, S.; Cheng, J.-P. Adv. Synth. Catal. 2010, 352, 1097; (j) Wada, S.-I.; Hitomi, T.; Tanaka, R. Helv. Chim. Acta 2009, 92, 1610; (k) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921; (l) Harrowven, D. C.; Lucas, M. C.; Howes, P. D. Tetrahedron 2001, 57, 791; (m) Fuerst, D. E.; Stolz, B. M.; Wood, J. L. Org. Lett. 2000, 2, 3521; (n) Onan, K. D.; Kelley, C. J.; Patarapanich, C.; Leary, J. D.; Aladesanmi, A. J. J. Chem. Soc., Chem. Commun. 1985, 121.
   PubMed Web of Science ®Google Scholar
• Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
   Web of Science ®Google Scholar
• Nicolaou, K. C.; Kang, Q.; Wu, T. R.; Lim, C. S.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 7540.
   PubMed Web of Science ®Google Scholar
• Piacente, S.; Montoro, P.; Oleszek, W.; Pizza, C. J. Nat. Prod. 2004, 67, 882.
   PubMed Web of Science ®Google Scholar
• Ramírez, M. L. G.; Trejo, A.; Navarro, V.; Bye, R.; Linares, E.; Delgado, G. J. Nat. Prod. 2001, 64, 432.
   PubMed Web of Science ®Google Scholar
• (a) Ingold, K. U.; Pratt, D. A. Chem. Rev. 2014, 114, 9022, and references cited therein; (b) Filippino, V.; Frenette, M.; Scaino, J. C. Org. Lett. 2009, 11, 3634; (c) Frenette, M.; MacLean, P. D.; Barclay, L. R. C.; Scaino, J. C. J. Am. Chem. Soc. 2006, 128, 16432.
   PubMed Web of Science ®Google Scholar
• (a) Chen, L.; Zhou, J. Chem. Asian J. 2012, 7, 2510; (b) Imato, K.; Nishihara, M.; Kanahara, T.; Amamoto, Y.; Takahara, A.; Otsuka, H. Angew. Chem., Int. Ed. 2012, 51, 1138; (c) Padwa, A.; Dehm, D.; Oine, T.; Lee, G. A. J. Am. Chem. Soc. 1975, 97, 1837.
   PubMed Web of Science ®Google Scholar
• (a) Chen, L.; Yin, X.-P.; Wang, C.-H.; Zhou, J. Org. Biomol. Chem. 2014, 12, 6033; (b) Shukla, P.; Choudhary, M. K.; Nayak, S. K. Synlett 2011, 1585.
   PubMed Web of Science ®Google Scholar
• (a) Zhu, X.-Q.; Zhou, J.; Wang, C.-H.; Li, X.-T.; Shajling J. Phys. Chem. B 2011, 115, 3588; (b) Li, X.; Hu, S.; Xi, Z.; Zhang, L.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2010, 75, 8697.
   PubMed Web of Science ®Google Scholar
• For recent references on bio-active spirocyclic benzofuran-2-ones, see (a) Pertino, M. W.; Theoduloz, C.; Rodríguez, J. A.; Lazo, V.; Yanez, Y.; Hirschmann, G-S. J. Nat. Prod. 2010, 73, 639; (b) Peŕez-Fons, L.; Garzoń, M. T.; Micol, V. J. Agric. Food Chem. 2010, 58, 161; (c) Nicolaou, K. C.; Wu, T. R.; Kang, Q.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2009, 48, 3440; (d) Ge, H. M.; Zhu, C. H.; Shi, D. H.; Zhang, L. D.; Xie, D. Q.; Yang, J.; Ng, S. W.; Tan, R. X. Chem. Eur. J. 2008, 14, 376; (e) Sontag, B.; Ruth, M.; Spiteller, P.; Arnold, N.; Steglich, W.; Reichert, M.; Bringmann, G. Eur. J. Org. Chem. 2006, 1023; (f) Yang, L.; Qin, L.-H.; Bligh, S. W. A.; Bashall, A.; Zhang, C.-F.; Zhang, M.; Wang, Z.-T.; Xu, L.-S. Bioorg. Med. Chem. 2006, 14, 3496.
   PubMed Web of Science ®Google Scholar
• Hernandez Alvarez, B.; Fischer, G.; Braun, M.; Hessamian-Alinejad, A.; Fliri, H. WO Patent 2003093258, 2003.
   Google Scholar
• (a) Wada, S.-I.; Hitomi, T.; Tokuda, H.; Tanaka, R. Chem. Biodiversity 2010, 7, 2303; (b) Guerrero, I. C.; Andres, L. S.; Leon, L. G.; Machin, R. P.; Padron, J. M.; Luis, J. G.; Delgadillo, J. J. Nat. Prod. 2006, 69, 1803.
   PubMed Web of Science ®Google Scholar
• Recent references on spirocyclic benzofuranone synthesis: (a) Li, X.; Lin, M.-H.; Han, Y.; Wang, F.; Cheng, J.-P. Org. Lett. 2014, 16, 114; (b) Albertshofer, K.; Tan, B.; Barbas, C. F. III. Org. Lett. 2013, 15, 2958; (c) Li, X.; Yang, C.; Jin, J.-L.; Xue, X.-S.; Cheng, J.-P. Chem.-Asian J. 2013, 8, 997; (d) Qi, L.-W.; Wang, L.-L.; Peng, L.; Jia, L.-N.; Tian, F.; Xu, X.-Y.; Wang, L.-X. Tetrahedron 2013, 69, 9303; (e) Li, X.; Wang, F.; Dong, N.; Cheng, J.-P. Org. Biomol. Chem. 2013, 11, 1451; (f) Cassani, C.; Tian, X.; Escudero-Adan, E. C.; Melchiorre, P. Chem. Commun. 2011, 47, 233.
   PubMed Web of Science ®Google Scholar
• Davies, S. G.; Foster, E. M.; McIntosh, C. R.; Roberts, P. M.; Rosser, T. E.; Smith, A. D.; Thomson, J. E. Tetrahedron: Asymmetry 2011, 22, 1035.
   Web of Science ®Google Scholar
• Li, Y.; Plesescu, M.; Prakash, S. R. Tetrahedron Lett. 2011, 52, 1807.
   Web of Science ®Google Scholar
• Kundu, K.; Tyagi, M.; Patro, B. S.; Chattopadhyay, S.; Nayak, S. K. Org. Commun. 2014, 7, 85.
   Web of Science ®Google Scholar