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一锅法合成 1,2-二氢吡啶:拓展炔丙基乙烯基醚的多样反应性。

One-pot synthesis of 1,2-dihydropyridines: expanding the diverse reactivity of propargyl vinyl ethers.

机构信息

Department Chemie and Catalysis Research Center, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.

出版信息

J Org Chem. 2011 Apr 1;76(7):2145-56. doi: 10.1021/jo102545m. Epub 2011 Mar 7.

Abstract

The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen rearrangement, a condensation step, and a Brønsted acid-catalyzed heterocyclization furnishes the highly substituted heterocycles in moderate to excellent yields. Additionally, a practical one-pot protocol toward 1,2-dihydropyridines and 2H-pyrans starting from propargylic alcohols was developed.

摘要

实现了从易得的丙炔基乙烯基醚出发催化合成 1,2-二氢吡啶。该反应序列涉及过渡金属催化的丙炔-Claisen 重排、缩合步骤和布朗斯台德酸催化的杂环化,以中等至优异的收率提供了高度取代的杂环。此外,还开发了一种从丙炔醇出发制备 1,2-二氢吡啶和 2H-吡喃的实用一锅法协议。

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