메뉴 건너뛰기




Volumn 45, Issue 9, 2004, Pages 1969-1972

1,3-Dipolar cycloadditions of azomethine ylides to alkenylboronic esters. Access to substituted boron analogues of β-proline and 3- hydroxypyrrolidines

Author keywords

Aminoacids analogues; Azomethine ylide; Boronic esters; Dipolar cycloaddition; Pyrrolidines

Indexed keywords

AZOMETHINE YLIDE; BORONIC ACID DERIVATIVE; ESTER; PROLINE; PYRROLIDINE DERIVATIVE;

EID: 1242338908     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.115     Document Type: Article
Times cited : (27)

References (56)
  • 5
    • 0037234688 scopus 로고    scopus 로고
    • and references cited therein
    • Adams J. Expert Opin. Ther. Pat. 13:2003;45. and references cited therein.
    • (2003) Expert Opin. Ther. Pat. , vol.13 , pp. 45
    • Adams, J.1
  • 19
    • 0042890348 scopus 로고    scopus 로고
    • For some references on synthesis and biological activities of substituted β-aminoboronates, see:
    • For some references on synthesis and biological activities of substituted β-aminoboronates, see: Hamilton G.H., Hughes C.E., Irving A.M., Vogels C., Westcott S.A. J. Organomet. Chem. 680:2003;143.
    • (2003) J. Organomet. Chem. , vol.680 , pp. 143
    • Hamilton, G.H.1    Hughes, C.E.2    Irving, A.M.3    Vogels, C.4    Westcott, S.A.5
  • 38
    • 85030890364 scopus 로고    scopus 로고
    • note
    • 4 (269.15): C, 58.01; H, 8.99; N, 5.20. Found: C, 57.6; H, 8.9; N, 4.8.
  • 39
    • 85030899908 scopus 로고    scopus 로고
    • note
    • + 344.20331, found 344.2056.
  • 43
    • 85030901752 scopus 로고    scopus 로고
    • note
    • 2O (50 mmol). The reaction mixture was refluxed for 12 h with removing of the formed water by means of a Dean Stark trap. A second addition of the same amount of formaldehyde was done after 2 h of reflux. The oil bath was removed and the mixture was then allowed to cool to room temperature. After filtration of the solid material, the filtrate was concentrated under reduced pressure. The residue was purified by distillation with Kügelrhor apparatus or by recrystallization.
  • 47
    • 85030898560 scopus 로고    scopus 로고
    • note
    • 3).
  • 48
    • 85030908252 scopus 로고    scopus 로고
    • As many boronic acids, compounds 5 tend to trimerize on standing.
  • 50
    • 85030913938 scopus 로고    scopus 로고
    • note
    • All attempts to prepare directly the NH derivative by using glycine and formaldehyde were unsuccessful.
  • 52
    • 85030907051 scopus 로고    scopus 로고
    • note
    • 3) (the resonance of the carbon α to boron was not detected).
  • 56
    • 85030902576 scopus 로고    scopus 로고
    • note
    • + 331.12422, found 331.1218.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.