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Volumn 44, Issue 25, 2003, Pages 4711-4714

A synthetic entry to 3,5-disubstituted pyridines

Author keywords

Acylation; Dihydropyridines; Oxidation; Pyridines

Indexed keywords

DIHYDROPYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE;

EID: 0038778499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01055-4     Document Type: Article
Times cited : (17)

References (31)
  • 7
    • 0035898722 scopus 로고    scopus 로고
    • See also: (c) Iida, T.; Wada, T.; Tomimoto, K.; Mase, T. Tetrahedron Lett. 2001, 42, 4841-4844; (d) Bonnet, V.; Mongin, F.; Trécourt, F.; Quéguiner, G.; Knochel, P. Tetrahedron 2002, 58, 4429-4438.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4841-4844
    • Iida, T.1    Wada, T.2    Tomimoto, K.3    Mase, T.4
  • 11
    • 0034660255 scopus 로고    scopus 로고
    • For recent examples of electrophilic substitutions from N-alkyl-3-acyl-1,4-dihydropyridines, see: (a) Lavilla, R.; Kumar, R.; Coll, O.; Masdeu, C.; Spada, A.; Bosch, J.; Espinosa, E.; Molins, E. Chem. Eur. J. 2000, 6, 1763-1772; (b) Kostyuk, A. N.; Volochnyuk, D. M.; Lupiha, L. N.; Pinchuk, A. M.; Tolmachev, A. A. Tetrahedron Lett. 2002, 43, 5423-5425.
    • (2000) Chem. Eur. J. , vol.6 , pp. 1763-1772
    • Lavilla, R.1    Kumar, R.2    Coll, O.3    Masdeu, C.4    Spada, A.5    Bosch, J.6    Espinosa, E.7    Molins, E.8
  • 12
    • 0037194188 scopus 로고    scopus 로고
    • For recent examples of electrophilic substitutions from N-alkyl-3-acyl-1,4-dihydropyridines, see: (a) Lavilla, R.; Kumar, R.; Coll, O.; Masdeu, C.; Spada, A.; Bosch, J.; Espinosa, E.; Molins, E. Chem. Eur. J. 2000, 6, 1763-1772; (b) Kostyuk, A. N.; Volochnyuk, D. M.; Lupiha, L. N.; Pinchuk, A. M.; Tolmachev, A. A. Tetrahedron Lett. 2002, 43, 5423-5425.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5423-5425
    • Kostyuk, A.N.1    Volochnyuk, D.M.2    Lupiha, L.N.3    Pinchuk, A.M.4    Tolmachev, A.A.5
  • 14
    • 0010404156 scopus 로고
    • For β-acylations of N-acyl-1,4-dihydropyridines, see: (c) Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703; (d) Comins, D. L.; Mantlo, N. B. Tetrahedron Lett. 1983, 24, 3683-3686.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3683-3686
    • Comins, D.L.1    Mantlo, N.B.2
  • 16
    • 37049110500 scopus 로고
    • The use of an easily removable trityl group was discarded as it is known that it is difficult to introduce at the nitrogen atom of 3-acylpyridines. See: Sammes M.-P., Lee C.-M., Katritzky A.R. J. Chem. Soc., Perkin Trans. 1. 1981;2476-2482.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 2476-2482
    • Sammes, M.-P.1    Lee, C.-M.2    Katritzky, A.R.3
  • 21
    • 0020393416 scopus 로고
    • N-Alkyldihydropyridines are usually oxidized to pyridinium salts, which are subsequently N-dealkylated. For an example, see: Wanner M.J., Koomen G.J., Pandit U.K. Tetrahedron. 38:1982;2741-2748.
    • (1982) Tetrahedron , vol.38 , pp. 2741-2748
    • Wanner, M.J.1    Koomen, G.J.2    Pandit, U.K.3
  • 24
    • 0011893718 scopus 로고
    • For previous syntheses of pyridine 2b, see: (a) McLean, S.; Murray, D. G. Can. J. Chem. 1972, 50, 1478-1485; (b) Jokela, R.; Tamminen, T.; Lounasmaa, M. Heterocycles 1985, 23, 1707-1723. See also Refs. 3 and 5a.
    • (1972) Can. J. Chem. , vol.50 , pp. 1478-1485
    • McLean, S.1    Murray, D.G.2
  • 25
    • 0000780738 scopus 로고
    • See also Refs. 3 and 5a
    • For previous syntheses of pyridine 2b, see: (a) McLean, S.; Murray, D. G. Can. J. Chem. 1972, 50, 1478-1485; (b) Jokela, R.; Tamminen, T.; Lounasmaa, M. Heterocycles 1985, 23, 1707-1723. See also Refs. 3 and 5a.
    • (1985) Heterocycles , vol.23 , pp. 1707-1723
    • Jokela, R.1    Tamminen, T.2    Lounasmaa, M.3
  • 26
    • 85031168814 scopus 로고    scopus 로고
    • note
    • 3), 70.2 (CH), 101.5 (C), 121.5 (CH), 122.3 (C), 126.0 (CH), 127.6-128.8 (CH), 138.6 (CH), 138.9 (C), 139.0 (C), 146.4 (C), 168.2 (C).
  • 27
    • 85031169269 scopus 로고    scopus 로고
    • note
    • 2: C, 74.67; H, 6.27; N, 5.81. Found: C, 74.84; H, 6.31; N, 5.69.
  • 30
    • 85031170215 scopus 로고    scopus 로고
    • note
    • D=-132 (c 1, MeOH).
  • 31
    • 85031167123 scopus 로고    scopus 로고
    • note
    • 4: 278.1260; found: 278.1263.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.