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Volumn 16, Issue 1, 2005, Pages 177-185

Synthesis of functionalized heterocycles via a tandem Staudinger/aza- Wittig/Ugi multicomponent reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMIDE; BRIDGED COMPOUND; HETEROCYCLIC COMPOUND; MORPHOLINE; PIPECOLIC ACID;

EID: 12344254694     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.079     Document Type: Article
Times cited : (70)

References (24)
  • 22
    • 12344325187 scopus 로고    scopus 로고
    • note
    • In an attempt to shorten the sequence of reactions we found that reaction of hemiacetal 2 with sodium azide gave rise to the formation of considerable amounts of 2,3-O-cyclohexylidene-1,4:1,5-dianhydro-d-ribose due to intramolecular displacement of the tosylate
  • 23
    • 12344330922 scopus 로고    scopus 로고
    • note
    • In initial studies aimed at optimizing the reaction conditions, we found that methanol proved to be superior to other solvents (dichloromethane, tetrahydrofuran) in the tandem process. Application of triphenylphosphine for the initial Staudinger step proved to be equally effective as trimethylphosphine. We elected to use the latter because the formed trimethylphosphine oxide can be easier removed from the reaction mixture than the corresponding triphenylphosphine oxide
  • 24
    • 0001304511 scopus 로고
    • Rotamers were assigned on the basis of EXSY experiments. For a review see: C.L. Perrin, and T.J. Dwyer Chem. Rev. 90 1990 935
    • (1990) Chem. Rev. , vol.90 , pp. 935
    • Perrin, C.L.1    Dwyer, T.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.