钯催化吲唑的C3和C7氧化直接烯基化反应：应用于加门唑的合成

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

作者信息

Naas Mohammed, El Kazzouli Saïd, Essassi El Mokhtar, Bousmina Mosto, Guillaumet Gérald

机构信息

Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR CNRS, 7311 , BP 6759, Orléans Cedex 2 45067, France.

Faculté des Sciences, Université Mohammed V de Rabat , BP 1014, Avenue Ibn Batouta, 10000 Rabat, Morocco.

出版信息

Org Lett. 2015 Sep 4;17(17):4320-3. doi: 10.1021/acs.orglett.5b02136. Epub 2015 Aug 26.

DOI:10.1021/acs.orglett.5b02136

PMID:26308587

Abstract

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.

摘要

本文描述了首例钯催化的(1H)-和(2H)-吲唑衍生物与各种烯烃的氧化烯基化反应。使用醋酸钯作为催化剂和碳酸银作为氧化剂，促进了(1H)-吲唑和(2H)-吲唑的选择性C3-单烯基化反应，以良好的产率得到所需产物。还开发了一种3-取代(1H)-吲唑的新颖氧化C7-烯基化反应。(1H)-吲唑的氧化烯基化反应以分步和原子经济的方式成功应用于候选药物加门达唑的全合成。