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Synthesis of Spiro Compounds through Tandem Oxidative Coupling and a Framework Rearrangement Reaction

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Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan, and Graduate School of Life and Environmental Science, Kyoto Prefectural University, Sakyo, Kyoto, 606-8522, Japan
[email protected]
†Kyoto University.
‡Kyoto Prefectural University.
Cite this: Org. Lett. 2010, 12, 2, 256–258
Publication Date (Web):December 10, 2009
https://doi.org/10.1021/ol902571p
Copyright © 2009 American Chemical Society
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Abstract

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A highly efficient oxidative coupling of 2-naphthols and a rearrangement tandem reaction to afford unique spiro compounds in the presence of FeCl3·6H2O in up to 88% yield have been developed.

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Full experimental details, characterization of all new compounds, and CIF of compound 3. This material is available free of charge via the Internet at http://pubs.acs.org.

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  23. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Zinc. 2017,,https://doi.org/10.1002/9780471264194.fos11455.pub5
  24. Louis F. Fieser, Mary Fieser, Tse‐Lok Ho. Fieser and Fieser's Reagents for Organic Synthesis. 2006,,https://doi.org/10.1002/9780471264194
  25. Tao Chen, Rui Peng, Wenxin Hu, Fu-Min Zhang. . Organic & Biomolecular Chemistry 2016,,, 9859. https://doi.org/10.1039/C6OB01733A
  26. Masaaki Yohda, Yasunori Yamamoto. Ruthenium–Me-BIPAM-catalyzed addition reaction of aryl-boronic acids to benzofuran-2,3-diones for the enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones. Tetrahedron: Asymmetry 2015, 26 (24) , 1430-1435. https://doi.org/10.1016/j.tetasy.2015.10.010
  27. Tao Deng, Hongjun Wang, Chun Cai. Copper-Catalyzed Asymmetric Oxidative Cross-Coupling of 2-Naphthols with Aryl Methyl Ketones. European Journal of Organic Chemistry 2015, 2015 (7) , 1569-1574. https://doi.org/10.1002/ejoc.201403512
  28. Fabrizio Vetica, Alessandra Pelosi, Augusto Gambacorta, M. Antonietta Loreto, Martina Miceli, Tecla Gasperi. Catalytic Friedel-Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold. European Journal of Organic Chemistry 2014, 2014 (9) , 1899-N1906. https://doi.org/10.1002/ejoc.201301686
  29. Tao Yin, Ruimao Hua. Straightforward Approach to Synthesize 3,3′-Bipyrroles by Oxidative Homocoupling of 1,2,5-Trisubstituted Pyrroles. Chemistry Letters 2013, 42 (8) , 836-837. https://doi.org/10.1246/cl.130253
  30. Tse-Lok Ho, Mary Fieser, Louis Fieser. Iron(III) Chloride. 2013,,, 291-295. https://doi.org/10.1002/9780471264194.fos11635.pub3
  31. Louis F. Fieser, Mary Fieser, Tse-Lok Ho. Fieser and Fieser's Reagents for Organic Synthesis. 2006,,https://doi.org/
  32. C. He, A. Lei. Application of Nontoxic Iron Salts in Oxidative CC Coupling Reactions. 2013,,, 521-547. https://doi.org/10.1016/B978-0-08-097774-4.00619-7
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  34. Rahim Ghadari, Fatemeh Hajishaabanha, Mojtaba Mahyari, Ahmad Shaabani, Hamid Reza Khavasi. An unexpected route toward the synthesis of spiro-benzo[b]acridine-furan derivatives. Tetrahedron Letters 2012, 53 (31) , 4018-4021. https://doi.org/10.1016/j.tetlet.2012.05.107
  35. Zhen Li, Jianquan Hong, Linhong Weng, Xigeng Zhou. Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides. Tetrahedron 2012, 68 (5) , 1552-1559. https://doi.org/10.1016/j.tet.2011.12.003
  36. Xiuli Bu, Jianquan Hong, Xigeng Zhou. Synthesis of Substituted Indenes through Iron-Catalyzed Annulation of Benzylic Alcohols with Alkynes. Advanced Synthesis & Catalysis 2011, 353 (11-12) , 2111-2118. https://doi.org/10.1002/adsc.201100065
  37. Ahmed Kamal, Y.V.V. Srikanth, M. Naseer A. Khan, Thokhir Basha Shaik, Md. Ashraf. Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorganic & Medicinal Chemistry Letters 2010, 20 (17) , 5229-5231. https://doi.org/10.1016/j.bmcl.2010.06.152
  38. Daisuke Sue, Takeo Kawabata, Takahiro Sasamori, Nobuhiro Tokitoh, Kazunori Tsubaki. ChemInform Abstract: Synthesis of Spiro Compounds Through Tandem Oxidative Coupling and a Framework Rearrangement Reaction.. ChemInform 2010, 41 (22) , no-no. https://doi.org/10.1002/chin.201022087

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