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Volumn 72, Issue 7, 2007, Pages 2364-2373

Cross-Diels-Alder reactions of 6-oxo-1-sulfonyl-1,6-dihydropyridine-3- carboxylates

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDUCTS; DIENOPHILES; HIGH PRESSURE ACTIVATION; INVERSE ELECTRON DEMAND (IED);

EID: 34047208734     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062186b     Document Type: Article
Times cited : (23)

References (71)
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    • For better readability, the generic name pyridones is used in this article, the case of pyridone 1a, rapid prototropy induces the formation of the more stable
    • For better readability, the generic name pyridones is used in this article. In the case of pyridone 1a, rapid prototropy induces the formation of the more stable 6-hydroxypyridine-3-carboxylate 3a.
    • 6-hydroxypyridine-3-carboxylate , vol.3 a
  • 28
    • 34047201467 scopus 로고    scopus 로고
    • 2O, MeOH, DMF, MeCN, AcOEt, and THF were used, without yielding any improvement.
    • 2O, MeOH, DMF, MeCN, AcOEt, and THF were used, without yielding any improvement.
  • 29
    • 34047238985 scopus 로고    scopus 로고
    • The transfer of the sulfonyl group from nitrogen to oxygen is probably disfavored under hyperbaric conditions. See ref 9 for various discussions on this type of process
    • The transfer of the sulfonyl group from nitrogen to oxygen is probably disfavored under hyperbaric conditions. See ref 9 for various discussions on this type of process.
  • 30
    • 0000164230 scopus 로고    scopus 로고
    • Biactivation by Lewis acids and high pressures has been reported to induce higher yields and selectivities. See: (a) Revial, G, Blanchard, M, d'Angelo, J. Tetrahedron Lett. 1983, 24, 899-902
    • Biactivation by Lewis acids and high pressures has been reported to induce higher yields and selectivities. See: (a) Revial, G.; Blanchard, M.; d'Angelo, J. Tetrahedron Lett. 1983, 24, 899-902.
  • 41
    • 0022523094 scopus 로고    scopus 로고
    • Interaction between the diene and the dienophile occurred exclusively from the less hindered, convex face of the latter; there are precedents in the literature for such behavior. See, for instance: (a) Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908-5919.
    • Interaction between the diene and the dienophile occurred exclusively from the less hindered, convex face of the latter; there are precedents in the literature for such behavior. See, for instance: (a) Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908-5919.
  • 46
    • 34047192728 scopus 로고    scopus 로고
    • Endo addition can be defined as that particular spatial arrangement of reactants in which the more bulky side of the diene is under the more bulky side of the dienophile, meaning the pyridone cycle in this case. See: Fringuelli, F.; Taticchi, A. In Dienes in the Diels-Alder Reaction; John Wiley and Sons Ltd.: New York, 1990; pp 1-44.
    • Endo addition can be defined as "that particular spatial arrangement of reactants in which the more bulky side of the diene is under the more bulky side of the dienophile", meaning the pyridone cycle in this case. See: Fringuelli, F.; Taticchi, A. In Dienes in the Diels-Alder Reaction; John Wiley and Sons Ltd.: New York, 1990; pp 1-44.
  • 47
    • 34047210386 scopus 로고    scopus 로고
    • Hydrolysis of the silyl enol ethers was carried out by stirring a methylene chloride solution of the subtrate in the presence of silica; see Experimental Section
    • Hydrolysis of the silyl enol ethers was carried out by stirring a methylene chloride solution of the subtrate in the presence of silica; see Experimental Section.
  • 54
    • 34047216382 scopus 로고    scopus 로고
    • Only dimerization of cyclopentadiene could be observed
    • Only dimerization of cyclopentadiene could be observed.
  • 58
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    • 4 catalysis, have been shown to yield inverse-electron-demand [4 + 2] heterocycloadducts, rather than normal-electron-demand [4 + 2] products. See: Denmark, S. E.; Kesley, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912-4924.
    • 4 catalysis, have been shown to yield inverse-electron-demand [4 + 2] heterocycloadducts, rather than normal-electron-demand [4 + 2] products. See: Denmark, S. E.; Kesley, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912-4924.
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    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford, U.K
    • Hill, R. K. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; pp 785-826.
    • (1991) Comprehensive Organic Chemistry , pp. 785-826
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  • 61
    • 34047240852 scopus 로고    scopus 로고
    • Molecular model inspection shows that the two double bonds in 12d-f are closer than those in 12a-c. Hence, the [3,3] sigmatropic rearrangement should be more favored from the IED cycloadducts obtained from cyclopentadiene, if the equilibrium is shifted towards the formation of the NED adducts
    • Molecular model inspection shows that the two double bonds in 12d-f are closer than those in 12a-c. Hence, the [3,3] sigmatropic rearrangement should be more favored from the IED cycloadducts obtained from cyclopentadiene, if the equilibrium is shifted towards the formation of the NED adducts
  • 62
    • 34047239258 scopus 로고    scopus 로고
    • It has to be kept in mind, however, that, in this precise case, an endo approach involving the s-trans conformer of dimethylbutadiene 4a would also allow stabilization of the secondary orbital interactions to take place, but would suffer from steric hindrance generated by the methyl groups as well. Such an approach would only give rise to IED endo cycloadduct 12a, and thus to the observed biscycloadduct 14a. Diagram presented
    • It has to be kept in mind, however, that, in this precise case, an endo approach involving the s-trans conformer of dimethylbutadiene 4a would also allow stabilization of the secondary orbital interactions to take place, but would suffer from steric hindrance generated by the methyl groups as well. Such an approach would only give rise to IED endo cycloadduct 12a, and thus to the observed biscycloadduct 14a. Diagram presented
  • 66
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    • For discussions on this topic, see: a
    • For discussions on this topic, see: (a) Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562-12571.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 12562-12571
    • Sustmann, R.1    Sicking, W.2
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    • Stout, D. M.; Yamamoto, D. M.; Barcelon-Yang, C. PCT International Application WO8601202, 1986.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.