A Practical, Metal-Free Synthesis of 1H-Indazoles

The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amen...

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Veröffentlicht in:Organic letters 2008-03, Vol.10 (5), p.1021-1023
Hauptverfasser: Counceller, Carla M, Eichman, Chad C, Wray, Brenda C, Stambuli, James P
Format: Artikel
Sprache:eng
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Zusammenfassung:The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800053f