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Volumn 47, Issue 5, 2006, Pages 631-634

InBr3-catalyzed intramolecular cyclization of 2-alkynylanilines leading to polysubstituted indole and its application to one-pot synthesis of an amino acid precursor

Author keywords

2 Ethynylaniline; Indium bromide; Indole; Intramolecular cyclization

Indexed keywords

AMINO ACID; ANILINE DERIVATIVE; BROMINE DERIVATIVE; FUNCTIONAL GROUP; IMINE; INDIUM; INDOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

EID: 29544433713     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.121     Document Type: Article
Times cited : (74)

References (69)
  • 2
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press San Diego
    • R.J. Sundberg Indoles 1996 Academic Press San Diego
    • (1996) Indoles
    • Sundberg, R.J.1
  • 47
    • 29544451393 scopus 로고    scopus 로고
    • note
    • 3 (0.025 mmol). The resulting mixture was refluxed and monitored by GC or TLC until the starting material was consumed. After the usual work-up, the crude product was purified by silica gel column chromatography to afford the 2-substituted indole 2a (91 mg, 95%) as a pale yellow solid.
  • 48
    • 29544436961 scopus 로고    scopus 로고
    • note
    • 3CN were not effective for the reaction.
  • 49
    • 29544448738 scopus 로고    scopus 로고
    • note
    • 3: 29%). Another group investigated a similar cyclization of an ethynylaniline derivative, see Ref. 3b.
  • 50
    • 29544443422 scopus 로고    scopus 로고
    • note
    • 4 = H), the corresponding indole product was not obtained under the present conditions.
  • 55
    • 29544447444 scopus 로고    scopus 로고
    • See Ref. 4.
    • See Ref. 4.
  • 56
    • 29544438355 scopus 로고    scopus 로고
    • note
    • 3: C, 64.28; H, 4.46; N, 6.52. Found: C, 64.28; H, 4.41; N, 6.43.
  • 57
    • 6244279150 scopus 로고
    • Although the role of TMSCl is not clear at this stage, it is known that a coexistence of Lewis acid and TMSCl promotes reactivity of an addition reaction, see: E.J. Corey, and N.W. Boaz Tetrahedron Lett. 26 1985 6015
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6015
    • Corey, E.J.1    Boaz, N.W.2
  • 66
    • 29544441482 scopus 로고    scopus 로고
    • note
    • 3 for the second step, the desired amino acid precursor 4a was produced in 57% yield.
  • 67
    • 0033930017 scopus 로고    scopus 로고
    • Selected papers for Lewis acid-promoted reaction of indole with imines, see: Y. Gong, K. Kato, and H. Kimoto Synlett 2000 1058
    • (2000) Synlett , pp. 1058
    • Gong, Y.1    Kato, K.2    Kimoto, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.