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Volumn 51, Issue 27, 2010, Pages 3565-3567

A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols

Author keywords

Copper; Cyclization; Furans; Heterocycles; Pyrroles

Indexed keywords

COPPER CHLORIDE; FURAN; PYRROLE;

EID: 77954244777     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.001     Document Type: Article
Times cited : (29)

References (72)
  • 20
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    • N. Asao Synlett 2006 1645 1656
    • (2006) Synlett , pp. 1645-1656
    • Asao, N.1
  • 31
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    • note
    • 3CCLi.
  • 32
    • 77954244022 scopus 로고    scopus 로고
    • note
    • 3CCMgBr, of the appropriate N-Boc-α-amino aldehyde, N-Boc-α-amino ester, or N-tosyl-α- amino ester (N-Boc-2-amino-3-phenylpropionaldehyde in the case of 1e; N-Boc-2-aminopropionaldehyde in the case of 1f; methyl N-Boc-2-aminopropionate in the case of 1g; methyl N-tosyl-2-aminopropionate in the case of 1h).
  • 42
    • 0347601791 scopus 로고    scopus 로고
    • The formation of pyrrole-2-carboxylate esters as by-products (0-29%) from N-tosyl-2-amino-3-hydroxy-4-ynoic esters in the presence of a stoichiometric amount of copper(I) acetate was reported some years ago: D.W. Knight, and C.M. Sharland Synlett 2004 119 121
    • (2004) Synlett , pp. 119-121
    • Knight, D.W.1    Sharland, C.M.2
  • 43
    • 0242659863 scopus 로고    scopus 로고
    • The formation of pyrrole-2-carboxylate esters by acid-promoted cyclization of N-tosyl-2-amino-3-hydroxy-4-ynoic esters (carried out in the presence of 0.5 equiv of TsOH) has been reported: D.W. Knight, and C.M. Sharland Synlett 2003 2258 2260
    • (2003) Synlett , pp. 2258-2260
    • Knight, D.W.1    Sharland, C.M.2
  • 45
    • 77954243389 scopus 로고    scopus 로고
    • note
    • 10 The yields obtained in each experiment are given in Tables 1 and 2.
  • 46
    • 77954242912 scopus 로고    scopus 로고
    • note
    • 2 (317.47): C, 75.67; H, 9.84; N, 4.41. Found: C, 75.75; H, 9.81; N, 4.43.
  • 47
    • 38749120651 scopus 로고    scopus 로고
    • Substituted furans and pyrroles are very important classes of heterocyclic compounds, which present a wide range of biological activity. For some recent reviews, see: H. Fan, J. Peng, M.T. Hamann, and J.-F. Hu Chem. Rev. 108 2008 264 287
    • (2008) Chem. Rev. , vol.108 , pp. 264-287
    • Fan, H.1    Peng, J.2    Hamann, M.T.3    Hu, J.-F.4
  • 54
    • 77954243448 scopus 로고    scopus 로고
    • For recent reviews on the synthesis of furans and pyrroles by heterocyclization approaches, see: Y. Lu, F. Song, X. Jia, and Y. Liu Prog. Chem. 22 2010 58 70
    • (2010) Prog. Chem. , vol.22 , pp. 58-70
    • Lu, Y.1    Song, F.2    Jia, X.3    Liu, Y.4
  • 61


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.