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Volumn 67, Issue 20, 2002, Pages 7144-7146

Synthesis of α-acyl-functionalized azacycles by Pd-catalyzed cross-coupling reactions of α-alkoxyboronates with lactam-derived vinyl triflates

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS;

EID: 0037019958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025930a     Document Type: Article
Times cited : (33)

References (36)
  • 16
    • 2142708085 scopus 로고    scopus 로고
    • note
    • Pd-catalyzed carbonylation of lactam-derived triflates might represent a general route (yet to be explored) for the incorporation of an acyl moiety. So far, Pd-catalyzed carbonylation has been applied to these systems only for the introduction of ester and amide groups (see ref 2b and references therein).
  • 18
    • 2142756726 scopus 로고    scopus 로고
    • note
    • 3) δ 5.30 (t, J = 3.5 Hz, 1 H), 3.78 (s, 3 H), 3.65 (m, 2 H), 2.26 (m, 2 H), 1.78 (m, 2 H).
  • 20
    • 2142769688 scopus 로고    scopus 로고
    • note
    • 13C NMR analysis: in the proton spectrum, the protons on C6 form an AX system with geminal coupling J = 15.8 Hz. Only one of the two protons couples significantly with 5-H (J = 6.6 Hz). The methyl group at position 5 resonates as a doublet (J = 7.0 Hz) due to the coupling with 5-H. In the carbon spectrum, a triplet at 42.8 ppm and a doublet at 33.4 are attributable to C6 and C5, respectively.
  • 21
    • 0000605285 scopus 로고
    • The initial double bond protonation that takes place in the formation of 8 is consistent with the proposed mechanism of γ-pyranone ring closure observed when substrates containing the same alkoxydienyl moiety were hydrolyzed. Prandi, C.; Venturello, P. J. Org. Chem. 1994, 54, 3494-3496.
    • (1994) J. Org. Chem. , vol.54 , pp. 3494-3496
    • Prandi, C.1    Venturello, P.2
  • 24
    • 0034704293 scopus 로고    scopus 로고
    • and references therein
    • (c) Giese, S.; West, F. G. Tetrahedron 2000, 56, 10221-10228 and references therein.
    • (2000) Tetrahedron , vol.56 , pp. 10221-10228
    • Giese, S.1    West, F.G.2
  • 25
    • 0025125371 scopus 로고
    • For example, the cyclization of 2-(3-methylbut-2-enoyl)indoles to give the corresponding cyclopenta[b]indolones occurred by heating at 110°C with polyphosphoric acid: Bergman, J.; Venemalm, L.; Gogoll, A. Tetrahedron 1990, 46, 6067-6084.
    • (1990) Tetrahedron , vol.46 , pp. 6067-6084
    • Bergman, J.1    Venemalm, L.2    Gogoll, A.3
  • 32
    • 2142647292 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the reaction mixtures, the =CH signal at 6.38 ppm of this olefin was diagnostic.
  • 33
    • 2142660161 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis) was attributable to the corresponding cyclic carbamate, but this was not isolated.
  • 34
    • 2142712496 scopus 로고    scopus 로고
    • note
    • -1.
  • 35
    • 2142763898 scopus 로고    scopus 로고
    • note
    • 3N to the eluant.
  • 36
    • 0037155539 scopus 로고    scopus 로고
    • A similar process has been reported very recently by Comins, although in that case the cyclization, which took place after addition of 12 to a double bond, gave rise to a six-membered cyclic carbamate: Williams, A. L.; Grillo, T. A.; Comins, D. L. J. Org. Chem. 2002, 67, 1972-1973.
    • (2002) J. Org. Chem. , vol.67 , pp. 1972-1973
    • Williams, A.L.1    Grillo, T.A.2    Comins, D.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.