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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 4
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Original Articles

Synthesis of 4-Alkoxy-N-Carboalkoxy-1,2-Dihydropyridines

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Pages 325-331 | Published online: 06 Dec 2006

References

  • Fowler , F. W. 1972 . J. Org. Chem. , 37 : 1321
  • Beeken , P. , Bonfiglio , J. N. , Haśan , I. , Piwinski , J. J. , Weinstein , B. , Zollo , K. A. and Fowler , F. W. 1979 . J. Am. Chem. Soc. , 101 : 6677 For recent uses of N-carboalkoxy-1,3-dihydropyridines in approaches to the total synthesis of natural products, see
  • Wender , P. A. , Schaus , J. M. and Torney , D. C. 1979 . Tetrahedron Lett. , : 2485
  • Mariano , P. S. , Dunaway-Mariano , D. and Huesman , P. L. 1979 . J. Org. Chem. , 44 : 124
  • Bonfiglio , J. N. , Hansan , I. , Piwinski , J. J. , Weinstein , B. and Fowler , F. W. 1976 . J. Am. Chem. Soc. , 98 : 2344
  • Haider , A. , Cornuz , G. and Wyler , H. 1975 . Helv. Chim. Acta , 58 : 1287
  • Beak , P. , Bonham , J. and Lee , J. T. Jr. 1968 . J. Am. Chem. Soc. , 90 : 1569 For an example of SN2 O-alkyl cleavage of 4-methoxypyridinium salts, see. For an example of SN2 O-alkyl cleavage of 4-methoxypyridine, see
  • Zoltewicz , J. A. and Sale , A. A. 1970 . J. Org. Chem. , 35 : 3462
  • 1H NMR (CDCl3) δ 2.53 (t, 2 H, J = 7 Hz, CH-2C=O), 3.87 (s, CO2CH-3) and 4.03 (t, J = 7 Hz, >NCH-2) total 5 H, 5.30 (d, 1 H, J = 8 Hz, >NCH=CH), 7.76 (d, 1 H, J = 8 Hz, >NCH=CH); mp 66–67°C
  • Katada , M. 1947 . J. Pharm. Soc. Japan , 67 : 61
  • Profft , E. , Krueger , W. , Kuhn , P. and Lietz , W. 1970 . Chem. Abs. , 72 : 90309w
  • Profft , E. and Schulz , G. 1961 . Arch. Pharm. , 294 : 292
  • Vompe , A. F. , Monich , N. V. and Meskhi , L. M. 1974 . Zh. Org. Khim. , 10 : 1296

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