Mild method for the synthesis of 1H-indazoles through oxime-phosphonium ion intermediate

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• 作者：Saurav Paul ; Subhankar Panda ; Debasis Manna ; ^{dmanna@iitg.ernet.in" class="auth_mail}
• 关键词：1H-Indazoles ; Oxime-phosphonium ion intermediate ; N&ndash ; N bond formation ; Mild reaction condition ; Basic medium
• 刊名：Tetrahedron Letters
• 出版年：9 April, 2014
• 年：2014
• 卷：55
• 期：15
• 页码：2480-2483
• 全文大小：2365 K

文摘

The synthesis of 1H-indazoles from o-aminobenzoximes is achieved via N-N bond formation using triphenylphosphine, I₂, and imidazole. Selective formation of oxime-phosphonium ion intermediate in the presence of the amino group is the driving force for this reaction. The nucleophilicity of the arylamino group and electrophilicity toward the N-O bond of oxime also control the reaction. The reaction proceeds at a faster rate with good to excellent yield under this mild reaction condition and is amenable to scale-up.