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Volumn 44, Issue 4, 2003, Pages 757-760

Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

3,6 DIHYDROPYRIDIN 2 ONE; 5 VINYLOXAZOLIDIN 2 ONE; N METHYLPYRIDIN 2 ONE; PALLADIUM; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037455038     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02677-1     Document Type: Article
Times cited : (24)

References (19)
  • 8
    • 0001219079 scopus 로고    scopus 로고
    • and references cited therein
    • The syn/anti assignment for the oxazolidinones is normally based on the size of the coupling between the 4- and 5-protons, which is known to be smaller for the anti isomers (in this case, 7.3 Hz for the syn isomer 3a, 5 Hz for the anti 3b). The proton at the 5-position is also known to resonate at higher field in the anti isomers (in this case δ 5.3 for 3a and δ 4.2 for 3b): see e.g. Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999-1015 and references cited therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 999-1015
    • Ibuka, T.1    Mimura, N.2    Aoyama, H.3    Akaji, M.4    Ohno, H.5    Miwa, Y.6    Taga, T.7    Nakai, K.8    Tamamura, H.9    Fujii, N.10
  • 9
    • 0032505212 scopus 로고    scopus 로고
    • Synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones employing ring-closing metathesis:
    • Synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones employing ring-closing metathesis: Sauriat-Dorizon H., Guibe F. Tetrahedron Lett. 39:1998;6711-6714.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6711-6714
    • Sauriat-Dorizon, H.1    Guibe, F.2
  • 17
    • 0012980778 scopus 로고    scopus 로고
    • note
    • 2Si requires 269.1818.
  • 18
    • 0012980779 scopus 로고    scopus 로고
    • 1H NMR resonances due to the vinyl protons of the 3,6-disubstituted pyridinones was found to be quite characteristic. In the 3,6-syn isomers, the two vinyl protons are very close in chemical shift (Δδ≈0.05 ppm), whereas in the 3,6-anti isomers, the chemical shift difference is greater (ca. 0.12 ppm). This difference helped to assign the stereochemistry of the piperidinones for which an unambiguous assignment was not available by other means (i.e. Table 1, entries 2, 3, 7, 9 and 10).
    • 1H NMR resonances due to the vinyl protons of the 3,6-disubstituted pyridinones was found to be quite characteristic. In the 3,6-syn isomers, the two vinyl protons are very close in chemical shift (Δδ≈0.05 ppm), whereas in the 3,6-anti isomers, the chemical shift difference is greater (ca. 0.12 ppm). This difference helped to assign the stereochemistry of the piperidinones for which an unambiguous assignment was not available by other means (i.e. Table 1, entries 2, 3, 7, 9 and 10).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.