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Volumn 8, Issue 14, 2010, Pages 3259-3266

Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

GOOD YIELD; ONE-POT SYNTHESIS; PROPARGYLIC ALCOHOLS;

EID: 77954565749     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c002093a     Document Type: Article
Times cited : (62)

References (34)
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    • Yang, B.V.1
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    • For a few selected examples, see:
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    • 3-catalyzed cycloaddition reaction of 3-sulfanylpropargyl alcohols or 3-selanylpropargyl alcohols with thioamides was reported. However, the substrates of this method are limited to the secondary aromatic 3-sulfanylpropargyl alcohols or secondary aromatic 3-selanylpropargyl alcohols. See:
    • T. Eicher and S. Hauptmann, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, Wiley-VCH, Weinheim, 2nd edn, 2003
    • (2003) The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications
    • Eicher, T.1    Hauptmann, S.2
  • 26
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    • Recently, the Nishibayashi team has tried to obtain the thiazoles by the reaction of propargylic alcohols with thiobenzamide in the presence of ruthenium and gold catalysts, but it was unsuccessful. See:
    • Y. -M. Pan F. -J. Zheng H. -X. Lin Z. -P. Zhan J. Org. Chem. 2009 74 3148
    • (2009) J. Org. Chem. , vol.74 , pp. 3148
    • Pan, Y.-M.1    Zheng, F.-J.2    Lin, H.-X.3    Zhan, Z.-P.4
  • 27
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    • 3-catalyzed propargylations and cycloaddition of 3-sulfanylpropargyl alcohols or 3-selanylpropargyl alcohols, γ-sulfanyl or γ-selanyl functional groups play an important role. Either the sulfur or the selenium atom stabilizes the propargyl cation and the allenyl cation, and promotes the propargylations and cycloaddition, e.g.
    • M. D. Milton Y. Inada Y. Nishibayashi S. Uemura Chem. Commun. 2004 2712
    • (2004) Chem. Commun. , pp. 2712
    • Milton, M.D.1    Inada, Y.2    Nishibayashi, Y.3    Uemura, S.4
  • 28
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    • 3-catalyzed nucleophilic substitution of propargylic alcohols with amides in acetonitrile affords the alkynyl-amides in good yields. See:
    • M. Yoshimatsu T. Otani S. Matsuda T. Yamamoto A. Sawa Org. Lett. 2008 10 4251
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    • The propargyl alcohols were prepared from aldehyde or ketone and alkyne. See:
    • M. Sato A. Yoshizawa Adv. Mater. 2007 19 4145
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    • Sato, M.1    Yoshizawa, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.