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Volumn 12, Issue 4, 2010, Pages 820-823

Efficient synthesis of α-ketoamides via 2-acyl-5-aminooxazoles by reacting acyl chlorides and α-isocyanoacetamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CHLORINATED HYDROCARBON; KETONE; NITRILE;

EID: 76849113146     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902894p     Document Type: Article
Times cited : (87)

References (44)
  • 1
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    • For recent reviews, see: (a) Dugave, C. Curr. Org. Chem. 2002, 6, 1397-1431.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 1397-1431
  • 6
    • 0027484224 scopus 로고
    • (a) Mehdi, S. Bioorg. Chem. 1993, 21, 249-259.
    • (1993) Chem. , vol.21 , pp. 249-259
    • Bioorg, M.S.1
  • 10
    • 33845555256 scopus 로고
    • See the following for examples, (a) Oxidation of α-aminoamides: Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1982, 104, 4446-4450.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4446-4450
    • Buckley, T.F.1    Rapoport, H.2
  • 11
  • 12
    • 33751157335 scopus 로고
    • (c) Oxidation of acyl cyanophosphoranes followed by amidation: Wasserman, H. H.; Ho, W. B. J. Org. Chem. 1994, 59, 4364-4366.
    • (1994) J. Org. Chem. , vol.59 , pp. 4364-4366
    • Wasserman, H.H.1    Ho, W.B.2
  • 14
    • 0033525476 scopus 로고    scopus 로고
    • (e) Ring opening and hydrolysis of azetidinones: Kim, S. K.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1827-1830.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1827-1830
    • Kim, S.K.1    Nuss, J.M.2
  • 35
    • 33845235189 scopus 로고
    • Other oxazoles syntheses starting from isocyanides and acyl chlorides are described in literature. See for example: (a) Suzuki, M.; Iwasaki, T.; Matsumoto, K.; Okumura, K. Synth. Commun. 1972, 2, 237-242.
    • (1972) Synth. Commun. , vol.2 , pp. 237-242
    • Suzuki, M.1    Iwasaki, T.2    Matsumoto, K.3    Okumura, K.4
  • 40
    • 76849096163 scopus 로고    scopus 로고
    • Better yields were obtained by using 37% HCl (1 h, 61% for 6a), instead of trifluoroacetic acid (32 h, 55% for 6a)
    • Better yields were obtained by using 37% HCl (1 h, 61% for 6a), instead of trifluoroacetic acid (32 h, 55% for 6a).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.