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Volumn 133, Issue 30, 2011, Pages 11430-11433

Expedient Synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; C-H BOND; EFFICIENT SYNTHESIS; ENAMIDES; ENAMINES; HETEROCYCLES;

EID: 79960887414     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203495c     Document Type: Article
Times cited : (268)

References (48)
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    • For recent reviews on C-H functionalization employing alkenes and alkynes, see
    • For recent reviews on C-H functionalization employing alkenes and alkynes, see: Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
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    • Satoh, T.1    Miura, M.2
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    • For leading references concerning the Rh(III)-catalyzed addition of C-H bonds to alkenes and alkynes, see
    • For leading references concerning the Rh(III)-catalyzed addition of C-H bonds to alkenes and alkynes, see: Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M. J. Org. Chem. 2011, 76, 13
    • (2011) J. Org. Chem. , vol.76 , pp. 13
    • Umeda, N.1    Hirano, K.2    Satoh, T.3    Shibata, N.4    Sato, H.5    Miura, M.6
  • 23
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    • Related transformations have been reported for the re-catalyzed imine-directed addition of isocyanates to electron-rich heterocycles: see ref 2c.
    • Related transformations have been reported for the re-catalyzed imine-directed addition of isocyanates to electron-rich heterocycles: see ref 2c.
  • 24
    • 79960857421 scopus 로고    scopus 로고
    • Typing the name of these drug and drug candidates into PubChem provides the compound structure, bioactivity, full list of literature, and access to ongoing clinical trials, applications, and usage: betrixaban (CID 10275777) and tariquidar (CID 148201).
    • Typing the name of these drug and drug candidates into PubChem provides the compound structure, bioactivity, full list of literature, and access to ongoing clinical trials, applications, and usage: betrixaban (CID 10275777) and tariquidar (CID 148201).
  • 25
    • 74949120125 scopus 로고    scopus 로고
    • For a recent report of the synthesis of N -acyl anthranilic acids by the Pd-catalyzed carboxylation of anilide C-H bonds with CO, see
    • For a recent report of the synthesis of N -acyl anthranilic acids by the Pd-catalyzed carboxylation of anilide C-H bonds with CO, see: Giri, R.; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 686
    • Giri, R.1    Lam, J.K.2    Yu, J.-Q.3
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    • 79960885927 scopus 로고    scopus 로고
    • Typing the name of these drugs into PubChem provides the compound structure, bioactivity, and access to ongoing clinical trials and applications: Tarceva (CID 176870) and Iressa (CID 123631).
    • Typing the name of these drugs into PubChem provides the compound structure, bioactivity, and access to ongoing clinical trials and applications: Tarceva (CID 176870) and Iressa (CID 123631).
  • 30
    • 78650879462 scopus 로고    scopus 로고
    • Enamides used in this study were readily prepared from the corresponding ketones
    • Enamides used in this study were readily prepared from the corresponding ketones: Guan, Z.-H.; Zhang, Z.-Y.; Ren, Z.-H.; Wang, Y.-Y.; Zhang, X. J. Org. Chem. 2011, 76, 339
    • (2011) J. Org. Chem. , vol.76 , pp. 339
    • Guan, Z.-H.1    Zhang, Z.-Y.2    Ren, Z.-H.3    Wang, Y.-Y.4    Zhang, X.5
  • 32
    • 79551654576 scopus 로고    scopus 로고
    • For recent examples of Rh(III)-catalyzed functionalization of vinylic C-H bonds of N -acetyl enamides with alkynes and alkenes, see
    • For recent examples of Rh(III)-catalyzed functionalization of vinylic C-H bonds of N -acetyl enamides with alkynes and alkenes, see: Huestis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 1338
    • Huestis, M.P.1    Chan, L.2    Stuart, D.R.3    Fagnou, K.4
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    • 2, see: Reference 2a.
    • 2, see: Reference 2a.
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    • Reference 3c.
    • Reference 3c.
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    • References 10b, 10c.
    • References 10b, 10c.
  • 40
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    • See Supporting Information.
    • See Supporting Information.
  • 44
    • 79960850101 scopus 로고    scopus 로고
    • Cyclization occurs more slowly for the less acidic N -hexyl or N -cyclohexyl amides obtained from alkyl isocyanates.
    • Cyclization occurs more slowly for the less acidic N -hexyl or N -cyclohexyl amides obtained from alkyl isocyanates.
  • 45
    • 84855676023 scopus 로고    scopus 로고
    • 2 in THF at 105 °C for 16 h.
    • 2 in THF at 105 °C for 16 h.
  • 46
    • 79955035089 scopus 로고    scopus 로고
    • Kinetic isotope effect studies for Rh(III)-catalyzed C-H/alkyne couplings have been shown to be consistent with rate-limiting C-H bond activation steps, see
    • Kinetic isotope effect studies for Rh(III)-catalyzed C-H/alkyne couplings have been shown to be consistent with rate-limiting C-H bond activation steps, see: Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 6449
    • Guimond, N.1    Gorelsky, S.I.2    Fagnou, K.3
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    • Reference 3a.
    • Reference 3a.
  • 48
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    • Reference 10b.
    • Reference 10b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.