Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones

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• 作者：Pan Li ; Chunrui Wu ; Jingjing Zhao ; Donald C. Rogness ; Feng Shi
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：April 6, 2012
• 年：2012
• 卷：77
• 期：7
• 页码：3149-3158
• 全文大小：431K
• 年卷期：v.77,no.7(April 6, 2012)
• ISSN：1520-6904

文摘

The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.