A facile synthesis of 4-acylamino-tetrahydroindazoles via the Ritter reaction

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• 作者：M膩ris Turks^a ; ^{maris_turks@ktf.rtu.lv} ; Inta Strakova^a ; Kirils Gorovojs^a ; Sergey Belyakov^b ; Yuri A. Piven^c ; Tatyana S. Khlebnicova^c ; Fedor A. Lakhvich^c
• 关键词：Tetrahydroindazoles ; Ritter reaction ; Amides ; Nitriles
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：5 August, 2012
• 卷：68
• 期：31
• 页码：6131-6140
• 文件大小：529 K

摘要

A new route toward 4-acylamino- and 4-amino-substituted tetrahydroindazoles is disclosed. The title聽compounds are obtained in good to excellent yields in the Ritter reaction between 4-hydroxy-tetrahydroindazoles and various nitriles. The reactivity of the tetrahydroindazole-derived carbenium ion is both sufficiently high to react with trichloroacetonitrile and sufficiently selective to resist the azide functionality within its structure. The present approach adds a method to the toolbox of tetrahydroindazole chemistry and facilitates the structural modifications of the scaffold, which has found important applications in medicinal chemistry.