Syntheses of Some 1,2- and 1,4-Dihydropyridines and X-Ray Crystal Structures of 1-Dimethylamino-5-ethoxycarbonyl-1,4-dihydro-3-methoxycarbonyl-2-methyl-4- phenylpyridine, 3-Cyano-3,4-dihydro-5-methoxycarbonyl-6-methyl-4-phenylpyridin-2(1H)-one and 5-Ethoxycarbonyl-1,4-dihydro-3-methoxycarbonyl-1,2-dimethyl-4-phenylpyridine

Journal of Chemical Research - Part S

Volumn , Issue 3, 1997, Pages 86-87

  Pendleton, Max D ^a   Beddoes, Roy L ^a   Andrew, Neil J ^a   Butters, Michael ^b   Joule, John A ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2542568186     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.1039/a607198h     Document Type: Article

References (21)

1. A. Hantzsch, Liebigs Ann. Chem., 1892, 215, 1.
2. F. Bossert, H. Meyer and E. Wehinger, Angew. Chem., Int. Ed. Engl., 1981, 20, 762; F. Bossert and W. Vater, Med. Res. Rev., 1989, 9, 291; S. Goldman and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 1991, 30, 1559; G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. DiMarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 1995, 38, 119.
3. F. Bossert, H. Meyer and E. Wehinger, Angew. Chem., Int. Ed. Engl., 1981, 20, 762; F. Bossert and W. Vater, Med. Res. Rev., 1989, 9, 291; S. Goldman and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 1991, 30, 1559; G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. DiMarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 1995, 38, 119.
4. F. Bossert, H. Meyer and E. Wehinger, Angew. Chem., Int. Ed. Engl., 1981, 20, 762; F. Bossert and W. Vater, Med. Res. Rev., 1989, 9, 291; S. Goldman and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 1991, 30, 1559; G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. DiMarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 1995, 38, 119.
5. F. Bossert, H. Meyer and E. Wehinger, Angew. Chem., Int. Ed. Engl., 1981, 20, 762; F. Bossert and W. Vater, Med. Res. Rev., 1989, 9, 291; S. Goldman and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 1991, 30, 1559; G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. DiMarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 1995, 38, 119.
6. K. Ohsumi, K. Ohishi, Y. Morinaga, R. Nakagawa, Y. Suga, T. Sekiyama, Y. Akiyama, T. Tsuji and T. Tsuruo, Chem. Pharm. Bull., 1995, 43, 818.
7. C. Ennis, S. E. Granger, V. C. Middlefell, M. E. Philpot and N. B. Shepperson, J. Cardiovasc. Pharmacol., 1989, 13, 511.
8. C. E. Sunkel, M. F. de Casa-Juana, L. Santos, M. M. Gómez, M. Villarroya, M. A. González-Morales, J. G. Priego and M. P. Ortega, J. Med. Chem., 1990, 33, 3205.
9. J. L. Archibald, G. Bradley, A. Opalko, T. J. Ward, J. C. White, C. Ennis and N. B. Shepperson, J. Med. Chem., 1990, 33, 646.
10. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
11. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
12. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
13. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
14. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
15. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
16. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
17. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
18. Key references are: W. Hanstein and K. Wallenfels, Tetrahedron, 1967, 23, 585; F. W. Fowler, J. Org. Chem., 1972, 37, 1321; E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans, 1, 1975, 929; E. E. Knaus and K. Redda, Can. J. Chem., 1977, 55, 1788; D. L. Comins and N. B. Mantlo, J. Org. Chem., 1986, 51, 5456; K. Wallenfels, H. Schuly and D. Hofmann, Liebigs Ann. Chem., 1959, 621, 106; W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978; J.-F. Biellmann and H. J. Callot, Bull. Soc. Chim. Fr., 1969, 1299; Y.-S. Wong, C. Marazano, D. Gnecco and B. C. Das, Tetrahedron Lett., 1994, 35, 707.
19. J. R. Pfister, Synthesis, 1990, 689.
20. G. M. Sheldrick, SHELX-86, Universities of York and Louvain, 1985.
21. TEXSAN-TEXRAY Structure Analysis Package, Molecular Structure Corporation, 1985.