The Preparation of 2-(4-Oxo-4H-1-benzopyran-2-yl)-1-phenyl-ethanones by the Condensation/Cyclization of Dilithiated 1-Benzoylacetone with Lithiated Methyl Salicylates

REFERENCES

• Beam , C. F. , Hines , M. A. , Mazat , C. L. , Duncan , D. C. , Beckman , D. D. , Lachicotte , R. J. , Tummons , R. C. and Heindel , N. D. 1989 . Chem. and Indust. (London) , : 727
   Google Scholar
• Livingston , M. L. , Chick , M. F. , Shealy , E. O. , Park , D. J. , Fulmer , T. D. and Beam , C. F. 1982 . J. Heterocycl. Chem. , 19 : 215
   Web of Science ®Google Scholar
• Beam , C. F. , Hall , H. L. , Huff , A. M. , Tummons , R. C. and O'Grady , S. A. 1984 . J. Heterocycl. Chem. , 21 : 1897
   Web of Science ®Google Scholar
• Mazat , C. L. , Beam , C. F. and Hines , M. A. 1990 . Synthetic Communications. , 20 : 253
   Web of Science ®Google Scholar
• Costa , A. M.B.S.R.C.S. , Dean , F. M. , Jones , M. A. , Sons , M. A. and Smith , D. A. 1986 . J. Chem. Soc., Perkin Trans. 1 , : 1707
   Google Scholar
• Hauser , C. R. and Harris , T. M. 1958 . J. Amer. Chem. Soc. , 80 : 6360
   Web of Science ®Google Scholar
• Light , R. J. and Hauser , C. R. 1960 . J. Org. Chem. , 25 : 538
   Google Scholar
• von Schrilz , D. M. , Miles , M. L. and Hauser , C. R. 1967 . J. Org. Chem. , 32 : 1774
   Google Scholar
• Hepworth , J. P. 1984 . “Comprehensive Heterocyclic Chemistry” , Edited by: Katritzky , A. R. and Rees , C. W. Vol. 3. , 816 – 830 . New York, New York : Board, Pergamon Press . Part 2B
   Google Scholar
• Rogalski , W. , Kirchlechner , R. , Seubert , J. , Gottschlich , R. , Steinieweg , R. , Bergmann , R. and Wahlig , H. Ger. Offen. DE . 2,442,829 . 1976 . Chem. Abstr. 1976, 85, P5501d.
   Google Scholar
• Eiden , F. , Rademacher , R. and Schuenemann , J. 1984 . Arch. Pharm. (Weinheim Ger.) , 317 : 539
   Google Scholar
• Nixon , N. S. , Scheinmann , F. and Suschitzky , J. L. 1983 . Tetrahedron Lett. , 24 : 597
   Google Scholar
• Bringmann , G. and Schneider , S. 1985 . Liebigs Ann. Chem. , : 765
   Google Scholar
• Jamura , Y. , Tsugoshi , T. , Morhi , S. and Kita , Y. 1985 . J. Org. Chem. , 50 : 1542
   Google Scholar
• Huang , F. C. , Campbell , H. F. , Learn , K. S. and Gammon , R. A. Jr. U.S. Patent, US . 4,977,162 . 1989 . Chem. Abstr. 1991 115, P8594k.
   Google Scholar
• Gammill , R. B. , Nash , S. A. , Bell , L. T. and Watt , W. 1992 . Tetrahedron Lett. , 33 : 993
   Google Scholar
• Morin , C. and Beugelmans , R. 1977 . Tetrahedron Lett. , 33 : 3183
   Google Scholar
• Doad , G. J.S. , Okar , D. I. , Scheinmann , F. , Bates , P. A. and Hursthouse , M. B. 1988 . J. Chem. Soc., Perkin Trans. 1 , : 22993
   Google Scholar
• 1-(2-hydroxy-4-methoxyphenyl)-5-phenyl-1,3,5-pentanetrione: Mp 187–89°C, 97% yield (ethanol): Anal. Calcd. for C18H16O5: C, 69.22; H, 5.16. Found: C, 69.18; H, 5.04; IR (paraffin oil) 1679 shoulder of broad and intense peaks from 1609–1627 cm−1; 1H NMR (CDCl3)(see ref. 7, first sentence): δ 3.90 (s, OCH3), 4.03 and 4.07 (s, -CH2-), 6.42 and 6.52 (s, vinyl), 6.58–7.15 and 7.50–8.33 (m, ArH)
   Google Scholar
• 1H-NMR were recorded on a Varian Associates EM-360L nuclear magnetic resonance spectrometer, and chemical shifts were recorded in δ ppm downfield from an internal tetramethylsilane (TMS) standard. Compd. No. (solvent) 1. (CDCl3): δ 4.45 (s, 2H, -CH2-), 6.48 (s, 1H, C3-H), and 7.36–8.70 (m, 9H, ArH). 2. (CDCl3): δ 3.93 (s, 3H, ArOCH3), 4.35 (s, 2H, -CH2-), 6.34 (s, 1H, C3-H), and 6.83–8.40 (m, 8H, ArH). 3. (CDCl3): δ 3.98 (s, 3H, ArOCH3), 4.38 (s, 2H, -CH2-), 6.40 (s, 1H, C3-H), and 7.25–8.28 (m, 8H, ArH). 4. (CDCl3/DMSO-d6): δ 4.55 (s, 2H, -CH2-), 6.55 (s, 1H, C3-H), and 7.30–8.38 (m, 8H, ArH). 5. (CDCl3) δ 4.40 (s, 2H, -CH2-), 6.48 (s, 1H, C3-H), and 7.18–8.52 (m, 8H, ArH). 6. (CDCl3/DMSO-d6): δ 4.70 (s, 2H, -CH2-), 6.68 (s, 1H, C3-H), and 7.54–8.48 (m, 7H, ArH). 7. (DMSO-d6): δ 4.93 (s, 2H, -CH2-), 6.67 (s, 1H, C3-H), and 7.67–8.76 (m, 7H, ArH). 8. (CDCl3/DMSO-d6): δ 4.45 (s, 2H, -CH2-), 6.50 (s, 1H, C3-H), and 7.20–8.85 (m, 8H, ArH). Integration for phenacyl methylene hydrogens averaged 2H, which depended upon solvent (sometimes less for DMSO-d6). See also: a. ref. 1b.
   Google Scholar
• Brown , J. , Sides , K. L. , Fulmer , T. D. and Beam , C. F. 1979 . J. Heterocycl. Chem. , 16 : 1669
   Google Scholar
• Huff , A. M. , Hall , H. L. , Smith , M. J. , O'Grady , S. A. , Waters , F. C. , Fengl , R. W. , Welch , J. A. and Beam , C. F. 1985 . J. Heterocycl. Chem. , 22 : 501
   Web of Science ®Google Scholar