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Volumn 13, Issue 14, 2011, Pages 3560-3563

Nickel-catalyzed synthesis of 1,3,5-trisubstituted hydantoins from acrylates and isocyanates

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; HYDANTOIN DERIVATIVE; ISOCYANIC ACID DERIVATIVE; NICKEL;

EID: 79960186286     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200957y     Document Type: Article
Times cited : (34)

References (32)
  • 13
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    • For recent examples of the synthesis of 1,3,5-substituted hydantoins without the use of transition-metal catalysts, see
    • For recent examples of the synthesis of 1,3,5-substituted hydantoins without the use of transition-metal catalysts, see: Sim, M. M.; Ganesan, A. J. Org. Chem. 1997, 62, 3230
    • (1997) J. Org. Chem. , vol.62 , pp. 3230
    • Sim, M.M.1    Ganesan, A.2
  • 23
    • 48349142260 scopus 로고    scopus 로고
    • Abbreviations: (S,S)- i -Pr-Foxap = (S,S)-[2-(4′-isopropyloxazolin- 2′-yl)ferrocenyl]diphenylphosphine. See:;, (S,S)-CHIRAPHOS = (2 S,3 S)-bis(diphenylphosphino)butane
    • Abbreviations: (S,S)- i -Pr-Foxap = (S,S)-[2-(4′-isopropyloxazolin- 2′-yl)ferrocenyl]diphenylphosphine. See: Miyake, Y.; Nishibayashi, Y.; Uemura, S. Synlett 2008, 1747 (S,S)-CHIRAPHOS = (2 S,3 S)-bis(diphenylphosphino) butane.
    • (2008) Synlett , pp. 1747
    • Miyake, Y.1    Nishibayashi, Y.2    Uemura, S.3
  • 25
    • 4244094395 scopus 로고
    • For β-hydride elimination of a five-membered ring azanicklacycle in anti mode, see
    • For β-hydride elimination of a five-membered ring azanicklacycle in anti mode, see: Hoberg, H.; Nohlen, M. J. Organomet. Chem. 1990, 382, C6
    • (1990) J. Organomet. Chem. , vol.382 , pp. 6
    • Hoberg, H.1    Nohlen, M.2
  • 26
    • 33947122173 scopus 로고    scopus 로고
    • Oxidative cyclization of 1-octene and cyclohexyl isocyanate catalyzed by a nickel(0)/IPr complex forms five-membered ring azanickelacycle, the alkene substituent (a hexyl group) of which is bound to a carbon β to nickel
    • Oxidative cyclization of 1-octene and cyclohexyl isocyanate catalyzed by a nickel(0)/IPr complex forms five-membered ring azanickelacycle, the alkene substituent (a hexyl group) of which is bound to a carbon β to nickel. Schleicher, K. D.; Jamison, T. F. Org. Lett. 2007, 9, 875
    • (2007) Org. Lett. , vol.9 , pp. 875
    • Schleicher, K.D.1    Jamison, T.F.2
  • 27
    • 27644500487 scopus 로고    scopus 로고
    • For related stablization, see
    • For related stablization, see: Duong, H. A.; Louie, J. J. Organomet. Chem. 2005, 690, 5098
    • (2005) J. Organomet. Chem. , vol.690 , pp. 5098
    • Duong, H.A.1    Louie, J.2
  • 30
    • 11444262868 scopus 로고    scopus 로고
    • Another mechanism consisting of intermolecular addition of NHC to isocyanate followed by conjugate addition of the resulting nitrogen anion to 4 and subsequent ring closure is also conceivable. For intermolecular addition of NHC to isocyanate, see
    • Another mechanism consisting of intermolecular addition of NHC to isocyanate followed by conjugate addition of the resulting nitrogen anion to 4 and subsequent ring closure is also conceivable. For intermolecular addition of NHC to isocyanate, see: Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679
    • (2004) Org. Lett. , vol.6 , pp. 4679
    • Duong, H.A.1    Cross, M.J.2    Louie, J.3
  • 31
    • 79960187896 scopus 로고    scopus 로고
    • N -Substituted fumaramates can be also prepared by half-esterification of fumaric acid with alcohols, followed by amidation with aniline derivatives. See the Supporting Information for details
    • N -Substituted fumaramates can be also prepared by half-esterification of fumaric acid with alcohols, followed by amidation with aniline derivatives. See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.