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Volumn 126, Issue 34, 2004, Pages 10546-10547

Intramolecular C-N bond addition of amides to alkynes using platinum catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMIDE; ANILIDE; CARBON; INDOLE DERIVATIVE; METAL; NITROGEN; PALLADIUM COMPLEX; PLATINUM; SOLVENT;

EID: 4344572110     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047542r     Document Type: Article
Times cited : (208)

References (30)
  • 1
    • 0003392387 scopus 로고    scopus 로고
    • Trost, B. M., Ed.; Thieme: Stuttgart
    • For reviews on the addition of nucleophiles to carbon-carbon multiple bonds, see: (a) Science of Synthesis; Trost, B. M., Ed.; Thieme: Stuttgart, 2001; Vol. 1.
    • (2001) Science of Synthesis , vol.1
  • 3
    • 0346265937 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (c) Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
  • 4
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (d) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4.
    • (1991) Comprehensive Organic Synthesis , vol.4
  • 7
    • 0002026596 scopus 로고    scopus 로고
    • Formal carboamination through the two-component coupling reactions has been developed. See: (a) Arcadi, A. Synlett 1997, 941-943.
    • (1997) Synlett , pp. 941-943
    • Arcadi, A.1
  • 14
    • 0028094766 scopus 로고
    • Acylindoles are also produced catalytically through the three-component coupling reactions using carbon monoxide. See: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803-11812.
    • (1994) Tetrahedron , vol.50 , pp. 11803-11812
    • Kondo, Y.1    Shiga, F.2    Murata, N.3    Sakamoto, T.4    Yamanaka, H.5
  • 16
    • 4344677512 scopus 로고    scopus 로고
    • note
    • The precise role of the solvent is not clear. However, we presume that the zwitterionic intermediate would be stabilized in electron-rich aromatics.
  • 17
    • 4344578215 scopus 로고    scopus 로고
    • note
    • We confirmed that deacylation from N-methylacetanilide hardly occurred under the same conditions (90% recovery, 16 h). This result clearly indicates that indoles 3 were not generated through the catalytic cyclization of 2-alkynylanilines that might be yielded via the deprotection of the starting materials.
  • 18
    • 4344708243 scopus 로고    scopus 로고
    • note
    • We confirmed that the reactions from both of these substrates proceeded simultaneously by monitoring thin-layer chromatography (TLC) and gas chromatography (GC-MS) analyses.
  • 22
    • 4344717930 scopus 로고    scopus 로고
    • See also ref 3f
    • (d) See also ref 3f.
  • 23
    • 2942557280 scopus 로고    scopus 로고
    • For reviews on the transition metal-catalyzed syntheses of heteroaromatic compounds, see: (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
    • (2004) Chem. Rev. , vol.104 , pp. 2127-2198
    • Nakamura, I.1    Yamamoto, Y.2
  • 26
    • 4344636186 scopus 로고    scopus 로고
    • See also ref 12c
    • (d) See also ref 12c.
  • 27
    • 0037603145 scopus 로고    scopus 로고
    • and references therein
    • Recently, our group also reported catalytic constructions of highly substituted indoles. See: Kamijo, S.; Yamamoto. Y. J. Org. Chem. 2003, 68, 4764-4771 and references therein.
    • (2003) J. Org. Chem. , vol.68 , pp. 4764-4771
    • Kamijo, S.1    Yamamoto, Y.2
  • 29
    • 0010653530 scopus 로고    scopus 로고
    • Thomas, E. J., Ed.; Georg Thieme Verlag: Stuttgart
    • (b) Joule, J. A. In Science of Synthesis; Thomas, E. J., Ed.; Georg Thieme Verlag: Stuttgart, 2000; Vol. 10, pp 361-652.
    • (2000) Science of Synthesis , vol.10 , pp. 361-652
    • Joule, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.