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Volumn 48, Issue 18, 2009, Pages 3288-3291

The regio- and stereoselective synthesis of trans-2,3-dihydropyridine n-oxides and piperidines

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIDINES; GRIGNARD REAGENT; HIGH YIELD; N-OXIDES; SEQUENTIAL ADDITION; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS;

EID: 70349913580     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900189     Document Type: Article
Times cited : (37)

References (22)
  • 3
    • 70349967434 scopus 로고    scopus 로고
    • Ring-opening does not occur when 3- or 3,5-methylpyridine N-oxide is reacted with Grignard reagents, instead pyridines are formed. See reference [3a].
    • c) Ring-opening does not occur when 3- or 3,5-methylpyridine N-oxide is reacted with Grignard reagents, instead pyridines are formed. See reference [3a].
  • 7
    • 70349950360 scopus 로고    scopus 로고
    • For rewievs, see
    • For rewievs, see:
  • 9
    • 0033709712 scopus 로고    scopus 로고
    • For other methods concerning piperidine synthesis, see
    • b) S. Laschat, T. Dickner, Synthesis 2000, 1781-1813. For other methods concerning piperidine synthesis, see:
    • (2000) Synthesis , pp. 1781-1813
    • Laschat, S.1    Dickner, T.2
  • 15
    • 70349943605 scopus 로고    scopus 로고
    • Reaction also performed in 10 mmol scale which gave 2 grams of 4a 72% yield
    • Reaction also performed in 10 mmol scale which gave 2 grams of 4a (72% yield).
  • 17
    • 70349969183 scopus 로고    scopus 로고
    • Nonius KappaCCD diffractometer (MoKα radiation λ, 0.71073 Å; T= 150(2)(1) K, Data collection: COLLECT (Nonius (1999, COLLECT. Nonius BV, Delft, The Netherlands, cell refinement: SCALEPACK (Macromolecular Crystallography, Part A: Z. Otwinowski, W. Minor, Methods in Enzymology, 276 (Eds, C. W. Carter, Jr, R. M. Sweet, Academic Press, New York, 1997, pp. 307, 326, data reduction: DENZO (Macromolecular Crystallography, Part A: Z. Otwinowski, W. Minor, Methods in Enzymology, 276 (Eds, C. W. Carter, Jr, R. M. Sweet, Academic Press, New York, 1997, pp. 307-326) and SCALEPACK; program(s) used to solve structure: SHELXS97 (G. M. Sheldrick, SHELXS97 and SHELXL97, University of Göttingen, Germany, 1997, All non-hydrogen atoms were refined anisotropically and hydrogen atoms by a riding model by full-matrix least-squares on F2. Program(s) used to refi
    • 2 (all data) = 0.2154. CCDC715909 (4i) and 715910 (4e) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 18
    • 70349928309 scopus 로고    scopus 로고
    • The diasteremeric ratio (d.r.) values were determined by NMR analysis of the crude reaction mixtures. The relative configuration was determined by the crystal structure of 4 i and 4 e and NMR analysis of the crystals, which proved to be the major isomer. Compounds assigned based upon comparison to 4 i and 4e and reported as major/minor: 4a 83:17,4b 82:12,4c 89:11,4d 89:11, 4e 88:12, 4f 72:28, 4g 78:22, 4h 90:10, 4i 50:50, 4j 60:40, 41 81:19 , 4m 79:21 , 4n 81:19, 4o 81:19.
    • The diasteremeric ratio (d.r.) values were determined by NMR analysis of the crude reaction mixtures. The relative configuration was determined by the crystal structure of 4 i and 4 e and NMR analysis of the crystals, which proved to be the major isomer. Compounds assigned based upon comparison to 4 i and 4e and reported as major/minor: 4a 83:17,4b 82:12,4c 89:11,4d 89:11, 4e 88:12, 4f 72:28, 4g 78:22, 4h 90:10, 4i 50:50, 4j 60:40, 41 81:19 , 4m 79:21 , 4n 81:19, 4o 81:19.
  • 19
    • 70349959466 scopus 로고    scopus 로고
    • A series of temperature experiments at -78, -40, -20, and 0°C. proved that - 20 °C. was the upper temperature limit. At temperatures above - 20 °C. a substantial amount of dienal oxime was observed.
    • A series of temperature experiments at -78, -40, -20, and 0°C. proved that - 20 °C. was the upper temperature limit. At temperatures above - 20 °C. a substantial amount of dienal oxime was observed.
  • 22
    • 70349928442 scopus 로고    scopus 로고
    • Compounds 3 and 7 were also accessible using Raney Nickel in 93 and 88 % yields, respectively.
    • Compounds 3 and 7 were also accessible using Raney Nickel in 93 and 88 % yields, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.