메뉴 건너뛰기




Volumn 133, Issue 15, 2011, Pages 5752-5755

Why do some fischer indolizations fail?

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLVATION; BOND CLEAVAGES; ELECTRON-DONATING SUBSTITUENTS; FISCHER INDOLE SYNTHESIS; MP2/6-31G; REACTION PATHWAYS; SIGMATROPIC REARRANGEMENTS;

EID: 79954467842     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201035b     Document Type: Article
Times cited : (52)

References (37)
  • 1
    • 0003979828 scopus 로고    scopus 로고
    • Ed.; Academic Press: London.
    • Indoles; Sundberg, R. J., Ed.; Academic Press: London, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 19
    • 50249176473 scopus 로고    scopus 로고
    • For synthetic studies involving psychotrimine and related alkaloids, see
    • For synthetic studies involving psychotrimine and related alkaloids, see: Newhouse, T.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 10886-10887
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10886-10887
    • Newhouse, T.1    Baran, P.S.2
  • 29
    • 79954498389 scopus 로고    scopus 로고
    • Employing substituted aryl hydrazines (e.g., p -OMe or o -Cl) did not lead to improvements.
    • Employing substituted aryl hydrazines (e.g., p -OMe or o -Cl) did not lead to improvements.
  • 31
    • 70450206724 scopus 로고    scopus 로고
    • revision A.2; Gaussian, Inc.: Wallingford, CT.
    • Frisch, M. J. Gaussian 09, revision A.2; Gaussian, Inc.: Wallingford, CT, 2009.
    • (2009) Gaussian 09
    • Frisch, M.J.1
  • 33
    • 79954536506 scopus 로고
    • Mann and Hinton (see:;) reported that the phenylhydrazone of 2-methyl-4-oxo-1,2,3,4-tetrahydroisoquinoline gave the 2-methyl-4- aminoisoquinolium salt when heated in ethanolic HCl, preventing the successful application of the Fischer indolization reaction. Cook and co-workers (11) obtained 4-amino-β-carboline derivatives along with Fischer indole products from the reaction of 2-benzoyl-4-oxo-1,2,3,4-tetrahydro-β-carboline with phenylhydrazine in ethanolic HCl
    • Mann and Hinton (see: Mann, F. G.; Hinton, I. G. J. Chem. Soc. 1959, 599-610) reported that the phenylhydrazone of 2-methyl-4-oxo-1,2,3,4- tetrahydroisoquinoline gave the 2-methyl-4-aminoisoquinolium salt when heated in ethanolic HCl, preventing the successful application of the Fischer indolization reaction. Cook and co-workers (11) obtained 4-amino-β- carboline derivatives along with Fischer indole products from the reaction of 2-benzoyl-4-oxo-1,2,3,4-tetrahydro-β-carboline with phenylhydrazine in ethanolic HCl
    • (1959) J. Chem. Soc. , pp. 599-610
    • Mann, F.G.1    Hinton, I.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.