DOI QR코드

DOI QR Code

Synergistic Effect of Pd(II) and Acid Catalysts on Tandem Annulation Reaction for the Regioselective Synthesis of Ring-Fused Quinolines

  • Ock, Su-Kyung (Department of Chemistry, Pukyong National University) ;
  • Youn, So-Won (Department of Chemistry, Hanyang University)
  • 발행 : 2010.03.20

초록

키워드

참고문헌

  1. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890. https://doi.org/10.1002/anie.200300634
  2. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365. https://doi.org/10.1021/cr950020x
  3. Tietze, L. F. Chem. Rev. 1996, 96, 115. https://doi.org/10.1021/cr950027e
  4. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65. https://doi.org/10.1016/S0022-328X(98)01052-3
  5. Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
  6. Youn, S. W. Eur. J. Org. Chem. 2009, 2597.
  7. Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302. https://doi.org/10.1039/b309033g
  8. Kamijo, S.; Sasaki, Y.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 35. https://doi.org/10.1016/j.tetlet.2003.10.141
  9. Wang, Y.; Peng, C.; Liu, L.; Zhao, J.; Su, L.; Zhu, Q. Tetrahedron Lett. 2009, 50, 2261. https://doi.org/10.1016/j.tetlet.2009.02.206
  10. Fu, W.; Xu, C.; Zou, G.; Hong, D.; Deng, D.; Wang, Z.; Ji, B. Synlett 2009, 763.
  11. Halim, R.; Scammells, P. J.; Flynn, B. L. Org. Lett. 2008, 10, 1967. https://doi.org/10.1021/ol800202u
  12. Sikorski, J. A. J. Med. Chem. 2006, 49, 1. https://doi.org/10.1021/jm058224l
  13. Bradburry, B. J.; Pucci, M. J. Curr. Opin. Pharm. 2008, 8, 574. https://doi.org/10.1016/j.coph.2008.04.009
  14. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166. https://doi.org/10.1039/b612168n
  15. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. https://doi.org/10.1021/ol034177k
  16. Pastine, S. J.; Youn, S. W.; Sames, D. Tetrahedron 2003, 59, 8859. https://doi.org/10.1016/j.tet.2003.05.003
  17. Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581. https://doi.org/10.1021/ol036385i
  18. Youn, S. W.; Eom, J. I. Org. Lett. 2005, 7, 3355. https://doi.org/10.1021/ol051264z
  19. Youn, S. W. J. Org. Chem. 2006, 71, 2521. https://doi.org/10.1021/jo0524775
  20. Youn, S. W. Org. Prep. Proced. Int. 2006, 38, 505. https://doi.org/10.1080/00304940609356447
  21. Youn, S. W.; Eom, J. I. J. Org. Chem. 2006, 71, 6705. https://doi.org/10.1021/jo061221b
  22. Youn, S. W. Synlett 2007, 3050.
  23. Youn, S. W.; Song, J.-H.; Jung, D.-I. J. Org. Chem. 2008, 73, 5658. https://doi.org/10.1021/jo800914c
  24. Youn, S. W.; Bihn, J. H. Tetrahedron Lett. 2009, 50, 4598. https://doi.org/10.1016/j.tetlet.2009.05.071

피인용 문헌

  1. Pd-Catalyzed Sequential CC and CN Bond Formations for the Synthesis of N-Heterocycles: Exploiting Protecting Group-Directed CH Activation under Modified Reaction Conditions vol.6, pp.8, 2011, https://doi.org/10.1002/asia.201100024
  2. One-Pot Synthesis of Furo- or Thienoquinolines through Sequential Imination and Intramolecular Palladium-Catalyzed Direct Arylation vol.2012, pp.34, 2012, https://doi.org/10.1002/ejoc.201201142
  3. An Efficient Synthesis of Substituted Quinolines via Indium(III) Chloride Catalyzed Reaction of Imines with Alkynes vol.33, pp.1, 2012, https://doi.org/10.5012/bkcs.2012.33.1.43
  4. Ru-Catalyzed Synthesis of Dihydrofuroquinolines from Azido-cyclopropyl Ketones vol.15, pp.6, 2013, https://doi.org/10.1021/ol400223d
  5. Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades vol.78, pp.10, 2013, https://doi.org/10.1021/jo400125p
  6. Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: switch of regioselectivity using an internal hydroxy group as a nucleophile vol.51, pp.71, 2015, https://doi.org/10.1039/C5CC05292K
  7. Lewis Acid Promoted Oxonium Ion Driven Carboamination of Alkynes for the Synthesis of 4-Alkoxy Quinolines vol.82, pp.4, 2017, https://doi.org/10.1021/acs.joc.6b02896
  8. -alkynylanilines with isocyanides triggered by intramolecular nucleopalladation: access to heterocyclic fused 2-aminoquinolines vol.54, pp.50, 2018, https://doi.org/10.1039/C8CC02028K
  9. ChemInform Abstract: Synergistic Effect of Pd(II) and Acid Catalysts on Tandem Annulation Reaction for the Regioselective Synthesis of Ring-Fused Quinolines. vol.41, pp.32, 2010, https://doi.org/10.1002/chin.201032160
  10. Sc(OTf)3‐Catalyzed Bicyclization of o‐Alkynylanilines with Aldehydes: Ring‐Fused 1,2‐Dihydroquinolines vol.126, pp.49, 2010, https://doi.org/10.1002/ange.201406959
  11. Sc(OTf)3‐Catalyzed Bicyclization of o‐Alkynylanilines with Aldehydes: Ring‐Fused 1,2‐Dihydroquinolines vol.53, pp.49, 2010, https://doi.org/10.1002/anie.201406959
  12. Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates vol.18, pp.23, 2010, https://doi.org/10.1021/acs.orglett.6b03151
  13. Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses vol.22, pp.23, 2010, https://doi.org/10.1021/acs.orglett.0c02898
  14. Silver-catalyzed tandem 5- and 6-endo-cyclizations via concomitant yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines vol.45, pp.35, 2010, https://doi.org/10.1039/d1nj02643g