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Volumn 75, Issue 8, 2010, Pages 2748-2751

Zinc chloride promoted formal oxidative coupling of aromatic aldehydes and isocyanides to α-ketoamides

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; GOOD YIELD; ISOCYANIDES; KETOAMIDES; OXIDATIVE COUPLINGS; ZINC CHLORIDE;

EID: 77951010597     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100302y     Document Type: Article
Times cited : (83)

References (114)
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    • For an excellent review on the oxidative transformation of aldehyde to esters and amides, see
    • For an excellent review on the oxidative transformation of aldehyde to esters and amides, see: Ekoue-Kovi, K.; Wolf, C. Chem. - Eur. J. 2008, 14, 6302
    • (2008) Chem. - Eur. J. , vol.14 , pp. 6302
    • Ekoue-Kovi, K.1    Wolf, C.2
  • 100
    • 65649085595 scopus 로고    scopus 로고
    • Examples of natural compounds
    • Examples of natural compounds: Carroll, A. R.; Avery, V. M. J. Nat. Prod. 2009, 72, 696
    • (2009) J. Nat. Prod. , vol.72 , pp. 696
    • Carroll, A.R.1    Avery, V.M.2
  • 102
    • 0034678615 scopus 로고    scopus 로고
    • Selected examples on Lewis acid-promoted/catalyzed Ugi-type reactions, see
    • Selected examples on Lewis acid-promoted/catalyzed Ugi-type reactions, see: Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1431
    • Oertel, K.1    Zech, G.2    Kunz, H.3
  • 110
    • 77950976732 scopus 로고    scopus 로고
    • The role of molecular sieves is less determinant related to conditions developed for aliphatic aldehydes (ref 17). Nevertheless, its presence increased significantly the yield of α-ketoamides, probably by accelerating the β-elimination step. After filtration, the α-ketoamides instead of α-iminoamides were the product that we detected by TLC
    • The role of molecular sieves is less determinant related to conditions developed for aliphatic aldehydes (ref 17). Nevertheless, its presence increased significantly the yield of α-ketoamides, probably by accelerating the β-elimination step. After filtration, the α-ketoamides instead of α-iminoamides were the product that we detected by TLC.
  • 111
    • 77950964838 scopus 로고
    • Addition of isocyanides to the boron trifluoride complex of nitrones has been reported to afford α-ketoamides in low yields (10?15%); see:,. We thank one of the reviewers for pointing out this important reference. Under our reaction conditions, the main side reaction was the subsequent Passerini reaction of the resulting α-ketoamides
    • Addition of isocyanides to the boron trifluoride complex of nitrones has been reported to afford α-ketoamides in low yields (10?15%); see: Zeeh, B. Synthesis 1969, 37. We thank one of the reviewers for pointing out this important reference. Under our reaction conditions, the main side reaction was the subsequent Passerini reaction of the resulting α-ketoamides.
    • (1969) Synthesis , pp. 37
    • Zeeh, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.