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路易斯酸催化的环丙烷醛和芳基肼的环合反应:四氢哒嗪的构建及其在一锅法合成六氢吡咯并[1,2-b]哒嗪中的应用。

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines.

机构信息

Department of Chemistry , Indian Institute of Technology Ropar , Nangal Road , Rupnagar , Punjab 140001 , India.

出版信息

J Org Chem. 2018 May 18;83(10):5438-5449. doi: 10.1021/acs.joc.8b00332. Epub 2018 May 2.

Abstract

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2- b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2- b]pyridazine was achieved with a good yield.

摘要

在本报告中,通过路易斯酸催化的环丙烷甲酰醛和芳基腙的环化反应,展示了四氢哒嗪的简便合成方法。此外,生成的四氢哒嗪进一步与供体-受体环丙烷发生环加成反应,生成六氢吡咯并[1,2-b]哒嗪。我们还以连续的方式在一锅法中进行了这两个步骤。此外,六氢吡咯并[1,2-b]哒嗪还实现了单脱羧反应,产率良好。

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