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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 5-6
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Original Articles

A Convenient Synthesis of 5-Aryltropones

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Pages 793-798 | Received 30 Jun 1988, Published online: 24 Oct 2006

References

  • Brossi , A. , Yeh , H. J. C. , Chrzanowska , M. , Wolff , J. , Hamel , E. , Lin , C. M. , Quin , F. , Suffness , M. and Silverton , J. 1988 . Medicinal Research Reviews , 8 : 77 – 94 . For a recent review, see:
  • Fitzgerald , T. J. 1976 . Biochem. Pharmacol. , 25 : 1383
  • Engelborghs , Y. and Fitzgerald , T. J. 1987 . J. Biol. Chem. , 262 : 5204 See, for example:
  • Nair , V. , Powell , D. W. and Suri , S. C. 1987 . Synth. Commun. , 17 : 1897
  • Pietra , F. 1973 . Chem. Rev. , 73 : 293
  • Heck , R. F. 1985 . Palladium Reagents in Organic Synthesis , Orlando : Academic Press .
  • Stang , P. J. , Hanack , M. and Subramanian , L. R. 1982 . Synthesis , : 85
  • Echavarren , A. M. and Stille , J. K. 1987 . J. Am. Chem. Soc. , 109 : 5478 Coupling with organostannanes:
  • Echavarren , A. M. and Stille , J. K. 1988 . J. Am. Chem. Soc. , 110 : 1557 Carbonylative coupling with organostannanes:
  • Chen , G. Y. and He , Y. B. 1987 . Tetrahedron Lett. , 28 : 2387 Coupling with alkyl- and alkynlzincs:
  • Cacchi , S. , Ciattini , P. J. , Morera , E. and Otar , G. 1986 . Tetrahedron Lett. , 27 : 5541 Reduction:
  • Dolle , R. E. , Schmidt , S. J. and Kruse , L. I. 1987 . J. Chem. Soc. Chem. Commun. , : 904 Alkoxycarbonylation
  • Oda , M. and Kitahara , Y. 1969 . Tetrahedron Lett. , : 3295
  • Russell , G. A. , Tanger , C. M. and Kosugi , Y. 1978 . J. Org. Chem. , 43 : 3278
  • 1H NMR (250 MHz, CDCl3): 7.23 (dd, 1H); 7.15 (dd, 1H); 7.07 (ddd, 1H); 6.61 (d, 1H); 3.99 (s, 3H). The regioisomer of 3, 2-[[(trifluoromethyl)sulfonyl]oxy]-5-methoxytropone, was also formed in 10% overall yield. As proof of the regiochemistry, palladium catalyzed reduction of 3 (Bu3N, HCO2H)8d gave 2-methoxytropone.
  • Bagli , J. F. , Bogri , T. , Palameta , B. and St-Jacques , M. 1979 . Can. J. Chem. , 57 1949
  • Nozoe , T. , Takase , K. , Saito , H. , Yamamoto , H. and Imafuku , K. 1986 . Chem. Lett. , : 1577 There is one other recent report of the synthesis of 5-aryltropolones

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