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Volumn 10, Issue 2, 2008, Pages 233-236

Electron-deficient dienes. 5. An inverse-electron-demand Diels-Alder approach to 2-substituted 4-methoxyxanthones and 3,4-dimethoxyxanthones

Author keywords

[No Author keywords available]

Indexed keywords

POLYENE; XANTHONE DERIVATIVE;

EID: 38749087284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702614b     Document Type: Article
Times cited : (64)

References (34)
  • 6
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    • This group has also recently reported xanthone synthesis via an aryl to imidazoyl migration process involving C-H activation
    • (a) Zhao, J.; Larock, R. C. Org. Lett. 2007, 72, 583. This group has also recently reported xanthone synthesis via an aryl to imidazoyl migration process involving C-H activation.
    • (2007) Org. Lett , vol.72 , pp. 583
    • Zhao, J.1    Larock, R.C.2
  • 10
    • 0032894356 scopus 로고    scopus 로고
    • IEDDA reactions of isomeric coumarin-fused electron deficient dienes with enamines 2 afforded benzocoumarins via a domino IEDDA / elimination / dehydrogenation sequence. See: Bodwell, G. J.; Pi, Z.; Pottie, I. R. Synlett 1999, 477.
    • IEDDA reactions of isomeric coumarin-fused electron deficient dienes with enamines 2 afforded benzocoumarins via a domino IEDDA / elimination / dehydrogenation sequence. See: Bodwell, G. J.; Pi, Z.; Pottie, I. R. Synlett 1999, 477.
  • 11
    • 38649143849 scopus 로고    scopus 로고
    • Mechanistically, this is an elimination reaction. Like all elimination reactions, it is an intramolecular reaction, but it differs from most others in that the reverse reaction is an intramolecular addition
    • Mechanistically, this is an elimination reaction. Like all elimination reactions, it is an intramolecular reaction, but it differs from most others in that the reverse reaction is an intramolecular addition.
  • 15
    • 0008999998 scopus 로고    scopus 로고
    • For the preparation of the ylide leading to 1d, see: Bell, T. W; Sondheimer, F. J. Org. Chem. 1981, 46, 217.
    • For the preparation of the ylide leading to 1d, see: Bell, T. W; Sondheimer, F. J. Org. Chem. 1981, 46, 217.
  • 17
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    • Jpn. Kokai Tokyo Koho, JP50052067
    • (a) Nohara, A.; Umetani, T.; Sanno, Y. Jpn. Kokai Tokyo Koho 1975, JP50052067.
    • (1975)
    • Nohara, A.1    Umetani, T.2    Sanno, Y.3
  • 19
    • 0022442643 scopus 로고    scopus 로고
    • For 11, see: Watanabe, M.; Hisamatsu, S.; Hotokezaka, H.; Furukawa, S. Chem. Pharm. Bull. 1986, 34, 2810.
    • For 11, see: Watanabe, M.; Hisamatsu, S.; Hotokezaka, H.; Furukawa, S. Chem. Pharm. Bull. 1986, 34, 2810.
  • 20
    • 0001725964 scopus 로고    scopus 로고
    • For the phosphonate leading to 1c, see: Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649.
    • For the phosphonate leading to 1c, see: Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649.
  • 21
    • 85027984620 scopus 로고    scopus 로고
    • For the phosphonate leading to 1e, see: Enders, D.; von Berg, S.; Jandeleit, B. Org. Synth. 2002, 78, 169.
    • For the phosphonate leading to 1e, see: Enders, D.; von Berg, S.; Jandeleit, B. Org. Synth. 2002, 78, 169.
  • 22
    • 38749084108 scopus 로고    scopus 로고
    • A stepwise reaction (Michael/Mannich) cannot be ruled out at this time, but we currently favor the asynchronous IEDDA pathway. More detailed commentary on this subject will be forthcoming.
    • A stepwise reaction (Michael/Mannich) cannot be ruled out at this time, but we currently favor the asynchronous IEDDA pathway. More detailed commentary on this subject will be forthcoming.
  • 23
    • 38749098050 scopus 로고    scopus 로고
    • For example, in the case of 17b, this H atom is part of a vinylogous malonate, i.e., glutaconate, system.
    • For example, in the case of 17b, this H atom is part of a vinylogous malonate, i.e., glutaconate, system.
  • 24
    • 38749118554 scopus 로고    scopus 로고
    • On the surface, this elimination doesn't appear to be disfavored in any way. In an AM1-calculated (ref 21) structure of 18f, a H-C-C-O dihedral angle of 164° at the site of elimination is predicted.
    • On the surface, this elimination doesn't appear to be disfavored in any way. In an AM1-calculated (ref 21) structure of 18f, a H-C-C-O dihedral angle of 164° at the site of elimination is predicted.
  • 25
    • 38749153148 scopus 로고    scopus 로고
    • The question arises of whether the reactions of dienes 1 with enamine 8 involve a similar rearrangement. Based on the evidence that is currently available, this possibility cannot be discounted.
    • The question arises of whether the reactions of dienes 1 with enamine 8 involve a similar rearrangement. Based on the evidence that is currently available, this possibility cannot be discounted.
  • 29
    • 38749136565 scopus 로고    scopus 로고
    • Chem3D, Version 5.0
    • Chem3D, Version 5.0.
  • 32
    • 38749111383 scopus 로고    scopus 로고
    • The intensity changes indicate that there are other (yet to be identified) nonradiative pathways that lower fm
    • m.
  • 33
    • 38749144677 scopus 로고    scopus 로고
    • o) energies, respectively.
    • o) energies, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.