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Volumn 10, Issue 12, 2012, Pages 2409-2412

One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation

Author keywords

[No Author keywords available]

Indexed keywords

ARYL TRIFLATES; HIGH YIELD; ONE POT; ONE-POT SYNTHESIS; TRIMETHYLSILYL;

EID: 84858017031     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob07117g     Document Type: Article
Times cited : (31)

References (21)
  • 6
    • 77957784497 scopus 로고    scopus 로고
    • For a review, see
    • E. S. Hsu Am. J. Ther. 2010 17 476
    • (2010) Am. J. Ther. , vol.17 , pp. 476
    • Hsu, E.S.1
  • 13
    • 79959687296 scopus 로고    scopus 로고
    • N-Tosylhydrazones have been alternatively employed as starting materials for the benzyne Fischer-indole reaction
    • P. Li J. Zhao C. Wu R. C. Larock F. Shi Org. Lett. 2011 13 3340
    • (2011) Org. Lett. , vol.13 , pp. 3340
    • Li, P.1    Zhao, J.2    Wu, C.3    Larock, R.C.4    Shi, F.5
  • 17
    • 0002977163 scopus 로고
    • 1H NMR spectroscopy. We have found that the hydrazone was fully converted to the chlorohydrazone 7a in about 30 minutes. We have also found that upon addition of CsF to the resulting reaction mixture, the chlorohydrazone 7a is instantly converted to its fluoro analogue 7a′ (supported by HRMS) For an explanation of the reactivity of the unsymmetrical monomethoxy benzyne, see
    • Y. Himeshima T. Sonoda H. Kobayashi Chem. Lett. 1983 1211
    • (1983) Chem. Lett. , vol.6 , pp. 1211
    • Himeshima, Y.1    Sonoda, T.2    Kobayashi, H.3
  • 20
    • 77950339557 scopus 로고    scopus 로고
    • Supporting the mechanism outlined in Scheme 2, GC/MS analysis of the crude reaction mixture for the preparation of 15a showed a peak (m/z = 113.1) corresponding to N-methylsuccinimide. Additionally, the absence of a peak (m/z = 264.32) corresponding to the dimerization product of compound 6a suggests that this reaction does not proceed through a [3 + 2] cycloaddition of an azomethyneimine and an aryne
    • P. H.-Y. Cheong R. S. Paton S. M. Bronner G.-Y. J. Im N. K. Garg K. N. Houk J. Am. Chem. Soc. 2010 132 1267
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1267
    • Cheong, P.H.-Y.1    Paton, R.S.2    Bronner, S.M.3    Im, G.-Y.J.4    Garg, N.K.5    Houk, K.N.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.