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Volumn 74, Issue 8, 2009, Pages 3148-3151

Brønsted acid-catalyzed propargylation/cycloisomerization tandem reaction: One-pot synthesis of substituted oxazoles from propargylic alcohols and amides

Author keywords

[No Author keywords available]

Indexed keywords

BI-FUNCTIONAL CATALYSTS; ONE POTS; ONE-POT SYNTHESIS; OXAZOLE; OXAZOLES; P-TOLUENE SULFONIC ACIDS; PROPARGYLIC ALCOHOLS; TANDEM PROCESS; TANDEM REACTIONS;

EID: 65249097391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8027533     Document Type: Article
Times cited : (143)

References (35)
  • 2
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    • and references cited therein
    • Winnik, M. A. Chem. Rev. 1981, 81, 491, and references cited therein.
    • (1981) Chem. Rev , vol.81 , pp. 491
    • Winnik, M.A.1
  • 7
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    • For recent reviews, see: a
    • For recent reviews, see: (a) Yeh, V. S. C. Tetrahedron 2004, 60, 11995.
    • (2004) Tetrahedron , vol.60 , pp. 11995
    • Yeh, V.S.C.1
  • 8
    • 0000314051 scopus 로고
    • (b) Wipf, P. Chem. Rev. 1995, 95, 2115.
    • (1995) Chem. Rev , vol.95 , pp. 2115
    • Wipf, P.1
  • 9
    • 65249176654 scopus 로고    scopus 로고
    • Palmer; D. C.; Venkatraman, S. In, The Chemistry of Heterocyclic Compounds, A Series of Monographs, Oxazoles: Synthesis, Reactions, and Spectroscopy Part A; Palmer, D. C, Ed.; John Wiley & Sons: Hoboken, NJ, 2003.
    • (c) Palmer; D. C.; Venkatraman, S. In, The Chemistry of Heterocyclic Compounds, A Series of Monographs, Oxazoles: Synthesis, Reactions, and Spectroscopy Part A; Palmer, D. C, Ed.; John Wiley & Sons: Hoboken, NJ, 2003.
  • 32
    • 65249093496 scopus 로고    scopus 로고
    • The zinc(II)-catalyzed propargylic substitution produces α-carbonyl amide. Subsequent cycloisomerization of a-carbonyl amide affords the substituted oxazole
    • The zinc(II)-catalyzed propargylic substitution produces α-carbonyl amide. Subsequent cycloisomerization of a-carbonyl amide affords the substituted oxazole.
  • 33
    • 65249181416 scopus 로고    scopus 로고
    • We have reported that the BiCl3-catalyzed nucleophilic substitution of propargylic alcohols with benzamide affords the alkynyl-amides in good yields, see ref 3d
    • 3-catalyzed nucleophilic substitution of propargylic alcohols with benzamide affords the alkynyl-amides in good yields, see ref 3d.
  • 34
    • 43849105745 scopus 로고    scopus 로고
    • 3) for a long time and fell off during workup. See: (a) Feng, X.-B.; Tan, Z.; Chen, D.; Shen, Y.-M.; Guo, C.-C.; Xiang, J.-N.; Zhu, C.-L. Tetrahedron Lett. 2008, 49, 4110.
    • 3) for a long time and fell off during workup. See: (a) Feng, X.-B.; Tan, Z.; Chen, D.; Shen, Y.-M.; Guo, C.-C.; Xiang, J.-N.; Zhu, C.-L. Tetrahedron Lett. 2008, 49, 4110.
  • 35
    • 65249190624 scopus 로고    scopus 로고
    • Reference 3a
    • (b) Reference 3a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.