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Volumn 46, Issue 5, 2005, Pages 767-770

Synthesis of regiospecifically substituted quinolines from anilines

Author keywords

Azaannulation; Formylation; Nitrogen heterocycles; Quinolines

Indexed keywords

ANILINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; N (TERT BUTYLOXYCARBONYL)ANILINE; N TERT BUTYLOXYCARBONYL 2 AMINOBENZALDEHYDE; PYRIDINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 12144273449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.020     Document Type: Article
Times cited : (21)

References (21)
  • 2
    • 0042730088 scopus 로고    scopus 로고
    • For recent works in this area, see: W. Du, and D.P. Curran Org. Lett. 5 2003 1765
    • (2003) Org. Lett. , vol.5 , pp. 1765
    • Du, W.1    Curran, D.P.2
  • 7
    • 12144252480 scopus 로고    scopus 로고
    • note
    • The 2-amino-3-fluorobenzaldehyde has been obtained in 55% yield by hydrolysis of the corresponding N-Boc derivative 3a (1,4-dioxane, HCl (3 N), 60°C, 3 h)
  • 9
    • 0012397313 scopus 로고
    • For a review on direct ortho metallation, see: V. Snieckus Chem. Rev. 90 1990 879
    • (1990) Chem. Rev. , vol.90 , pp. 879
    • Snieckus, V.1
  • 13
    • 0000746580 scopus 로고
    • N-Boc anilines 2a-c were prepared by heating at 60°C the required aniline with di-tert-butyl dicarbonate in a THF solution for 15 h as described: J.M. Muchowski, and M.C. Venuti J. Org. Chem. 45 1980 4798
    • (1980) J. Org. Chem. , vol.45 , pp. 4798
    • Muchowski, J.M.1    Venuti, M.C.2
  • 14
    • 12144277006 scopus 로고    scopus 로고
    • note
    • 3: C, 60.24; H, 5.90; N, 5.85. Found: C, 60.34; H, 5.86; N, 5.89
  • 16
    • 12144256758 scopus 로고    scopus 로고
    • note
    • 3N: C, 66,39; H, 5,57; N, 5,53.
  • 20
    • 1442335425 scopus 로고    scopus 로고
    • For applications of acridine derivatives, see: J. Chiron, and J.-P. Galy Synthesis 2004 313 and references therein
    • (2004) Synthesis , pp. 313
    • Chiron, J.1    Galy, J.-P.2
  • 21
    • 0002747589 scopus 로고    scopus 로고
    • A very interesting one-pot procedure has been developed by for the synthesis of quinoline and 1,2,3,4-tetrahydroacridine derivatives. The method is based on the formylation of ortho-dilithiated N-pivaloylanilines followed by treatment with carbonyl compounds and KHMDS. However, the method failed when 2-methycyclohexanone was used as the carbonyl component J.I. Úbeda, M. Villacampa, and C. Avendaño Synthesis 1998 1176
    • (1998) Synthesis , pp. 1176
    • Úbeda, J.I.1    Villacampa, M.2    Avendaño, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.