DOI QR코드

DOI QR Code

Expedient Syntheses of Unsymmetrical 4-Bromo-2-carboxyl-biaryls via Diels-Alder Cycloadditions of 3,5-Dibromo-2-pyrone with Vinyl Arenes, Followed by One Pot, Three Step Aromatization Reactions


Abstract

Keywords

References

  1. Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. https://doi.org/10.1016/S0040-4020(00)00940-6
  2. Cortez, D. A. G.; Young, M. C. M.; Marston, A.; Wolfender, J.-L.; Hostettmann, K. Phytochemistry 1998, 47, 1367. https://doi.org/10.1016/S0031-9422(97)00731-0
  3. Pascal, C.; Dubois, J.; Guenard, D.; Gueritte, F. J. Org. Chem. 1998, 63, 6414. https://doi.org/10.1021/jo980697v
  4. Schmidt, U.; Leitenberger, V.; Griesser, H.; Schmidt, J.; Meyer, R. Synthesis 1992, 1248.
  5. Setayesh, S.; Grimsdal, A. C.; Weil, T.; Enkelmann, V.; Mullen,K.; Meghdadi, F.; List, E. J. W.; Leising, G. J. Am. Chem. Soc.2001, 123, 946. https://doi.org/10.1021/ja0031220
  6. Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699. https://doi.org/10.1021/jo016131f
  7. Shen, W.; Fakhoury, S.; Donner, G.; Henry, K.; Lee, J.; Zhang, H.; Cohen, J.; Warner, R.; Saeed, B.; Cherian, S.; Tahir, S.; Kovar, P.; Bauch, J.; Ng, S.-C.; Marsh, K.; Sham, H.; Rosenberg, S. Bioorg. Med. Chem. Lett. 1999, 9, 703. https://doi.org/10.1016/S0960-894X(99)00080-3
  8. Chen, M.-H.; Pollard, P. P.; Patchett, A. A. Bioorg. Med. Chem. Lett. 1999, 9, 1261. https://doi.org/10.1016/S0960-894X(99)00183-3
  9. Yin, Y.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162. https://doi.org/10.1021/ja017082r
  10. Neustadt, B. R.; Smith, E. M.; Lindo, N.; Nechuta, T.; Bronnenkant, A.; Wu, A.; Armstrong, L.; Kumar, C. Bioorg. Med. Chem. Lett. 1998, 8, 2395. https://doi.org/10.1016/S0960-894X(98)00433-8
  11. Lee, J.-H.; Park, J.-S.; Cho, C.-G. Org. Lett. 2002, 4, 1171. https://doi.org/10.1021/ol025613q
  12. Cho, C.-G.; Kim, Y.-W.; Lim, Y.-K.; Park, J.-S.; Lee, H. J. Org. Chem. 2001, 67, 290. https://doi.org/10.1021/jo015804r
  13. Cho, C.-G.; Park, J.-S.; Jung, I.-H.; Lee, H. Tetrahedron Lett. 2001, 42, 1065. https://doi.org/10.1016/S0040-4039(00)02182-1
  14. Cho, C.-G.; Kim, Y.-W.; Kim, W.-K. Tetrahedron Lett. 2001, 42, 8193. https://doi.org/10.1016/S0040-4039(01)01760-9

Cited by

  1. Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones vol.8, pp.15, 2006, https://doi.org/10.1021/ol061198g
  2. ChemInform Abstract: Expedient Syntheses of Unsymmetrical 4-Bromo-2-carboxyl-biaryls via Diels-Alder Cycloadditions of 3,5-Dibromo-2-pyrone with Vinyl Arenes, Followed by One-Pot, Three-Step Aromatization Reactions. vol.33, pp.48, 2010, https://doi.org/10.1002/chin.200248092
  3. High-Pressure-Promoted Diels–Alder Approach to Biaryls: Application to the Synthesis of the Cannabinols Family vol.77, pp.18, 2012, https://doi.org/10.1021/jo301203k
  4. Theoretical insights into the [4 + 2]/retro [4 + 2] cycloaddition approach to the synthesis of biaryls and polycyclic aromatics vol.56, pp.5, 2013, https://doi.org/10.1007/s11426-012-4821-5
  5. Recent Advances in the Synthesis of 2-Pyrones vol.13, pp.3, 2015, https://doi.org/10.3390/md13031581
  6. Diels–Alder Approach to Polysubstituted Biaryls: Rapid Entry to Tri- and Tetra-ortho-substituted Phosphorus-Containing Biaryls vol.118, pp.40, 2006, https://doi.org/10.1002/ange.200602683
  7. Diels–Alder Approach to Polysubstituted Biaryls: Rapid Entry to Tri- and Tetra-ortho-substituted Phosphorus-Containing Biaryls vol.45, pp.40, 2006, https://doi.org/10.1002/anie.200602683
  8. Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes vol.43, pp.50, 2002, https://doi.org/10.1016/s0040-4039(02)02305-5
  9. Synthesis of tetrahydrofluorenes from the cycloadduct of 3-ethynyl-5-bromo-2-pyrone via cyclocarbopalladation reactions vol.44, pp.24, 2003, https://doi.org/10.1016/s0040-4039(03)01032-3
  10. Tandem or Sequential Coupling−IMDA Cycloaddition Approach to Highly Fused Polycarbocycles vol.68, pp.26, 2002, https://doi.org/10.1021/jo035354y
  11. Diels–Alder approach to biaryls (DAB): Importance of the ortho-nitro moiety in the [4 + 2] cycloaddition vol.6, pp.2, 2002, https://doi.org/10.1039/b714893c
  12. Synthesis of Functionalized Aromatic Carboxylic Acids from Biosourced 3-Hydroxy-2-pyrones through a Base-Promoted Domino Reaction vol.8, pp.30, 2002, https://doi.org/10.1021/acssuschemeng.0c02290
  13. Emergence of 2-Pyrone and Its Derivatives, from Synthesis to Biological Perspective: An Overview and Current Status vol.379, pp.6, 2002, https://doi.org/10.1007/s41061-021-00350-w