Palladium-Catalyzed Oxidative Direct C3- and C7-Alkenylations of Indazoles: Application to the Synthesis of Gamendazole

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• 作者：Mohammed Naas ; Sa茂d El Kazzouli ; El Mokhtar Essassi ; Mosto Bousmina ; G茅rald Guillaumet
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：17
• 期：17
• 页码：4320-4323
• 全文大小：380K
• ISSN：1523-7052

文摘

The first palladium-catalyzed oxidative alkenylation of (1H)- and (2H)-indazole derivatives with various olefins is described. The use of Pd(OAc)₂ as the catalyst and Ag₂CO₃ as the oxidant promoted the selective C3-monoalkenylation of (1H)-indazoles and (2H)-indazoles, affording the desired products in good yields. An original oxidative C7-alkenylation of 3-substituted (1H)-indazoles was also developed. The oxidative alkenylation of (1H)-indazole was successfully applied to the total synthesis of the drug candidate gamendazole in a step- and atom-economical fashion.