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Volumn 52, Issue 29, 2013, Pages 7509-7513

Base-catalyzed synthesis of substituted indazoles under mild, transition-metal-free conditions

Author keywords

heterocycles; hydrazones; indazoles; N arylation; synthetic methods

Indexed keywords

HETEROCYCLES; HYDRAZONES; INDAZOLES; N-ARYLATIONS; SYNTHETIC METHODS;

EID: 84880106330     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300917     Document Type: Article
Times cited : (102)

References (68)
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    • Xiao, Q.1    Zhang, Y.2    Wang, J.3
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    • [8c] involved the use of copper bromide, special care was taken in the purification of product 1 aa. We also tried to keep potential metal contamination as low as possible in other reactions (see also Ref. [18]). For a review related to these issues, see:, I. Thomé, A. Nijs, C. Bolm, Chem. Soc. Rev. 2012, 41, 979.
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    • Thomé, I.1    Nijs, A.2    Bolm, C.3
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    • The isomer ratio was determined by NMR spectroscopy and HPLC analysis, and the respective data were compared with those reported in Ref. [7e]; see also:, C. A. Bunnell, P. L. Fuchs, J. Org. Chem. 1977, 42, 2614.
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    • For an analogous photoisomerization of N,N-dimethylhydrazones, see:, L. F. Clarke, F. O'Sullivan, A. F. Hegarty, J. Chem. Soc. Perkin Trans. 2 1991, 1649. Attempts to promote the isomerization and cyclization of the E isomer of 1 aa and the corresponding starting material for the formation of 2 l by exposure to UV irradiation failed and resulted in decomposition of the starting materials.
    • (1991) J. Chem. Soc. Perkin Trans. 2 , pp. 1649
    • Clarke, L.F.1    O'Sullivan, F.2    Hegarty, A.F.3
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    • The observed signal is centered at g=2.012. This value falls outside the range expected for hydrazyl (2.0032-2.0038) as well as for σ or π aryl anion radicals [2.0020-2.0025 and 2.0026-2.0029, respectively: Electron Spin Resonance Spectroscopy of Organic Radicals (Eds.:, F. Gerson, W. Huber,), Wiley-VCH, Weinheim, 2003 ]. The higher g value, however, is not unexpected owing to the diradical nature of the postulated intermediate. The broadness of the signal caused by the solid state of the species precludes any quantitative determination of zero-field splitting or hyperfine coupling.
    • (2003) Electron Spin Resonance Spectroscopy of Organic Radicals


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