Synthesis of 3-substituted indazoles from arynes and N-tosylhydrazones

Organic Letters

Volumn 13, Issue 13, 2011, Pages 3340-3343

  Li, Pan ^a   Zhao, Jingjing ^a   Wu, Chunrui ^a   Larock, Richard C ^b   Shi, Feng ^a  

^a HENAN UNIVERSITY   (China)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; INDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

HYDRAZONES; INDAZOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79959687296     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201086g     Document Type: Article

References (37)

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35. From Hammond's postulate and a soft-hard acid-base argument, we consider the other resonance structure of the conjugate base, where the negative charge resides on the imine carbon, as a less important structure to participate in the reaction. A brief computational study of benzaldehyde N -mesylhydrazone as a simplified system on a B3LYP/6-31G(d) level reveals that the nitrogen carries a much more negative charge (-0.494 vs -0.065 for the carbon), and therefore the reaction with a highly reactive agent, such as benzyne, should occur more favorably at the nitrogen, rather than at the carbon.
36. See the Supporting Information for the NOESY spectrum.
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