Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

Lan-Gui Xie; Saad Shaaban; Xiangyu Chen; Nuno Maulide

doi:10.1002/anie.201606604

Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

Angew Chem Int Ed Engl. 2016 Oct 4;55(41):12864-7. doi: 10.1002/anie.201606604. Epub 2016 Sep 14.

Authors

Lan-Gui Xie¹, Saad Shaaban¹, Xiangyu Chen¹, Nuno Maulide²

Affiliations

¹ University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090, Vienna, Austria.
² University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090, Vienna, Austria. nuno.maulide@univie.ac.at.

PMID: 27623988
DOI: 10.1002/anie.201606604

Abstract

The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Brønsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.

Keywords: alkynes; cycloaddition; heteroalkynes; nitriles; pyridines.

Publication types

Research Support, Non-U.S. Gov't