Organic Chemistry Portal

Abstracts

Search:

Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines

Ivan A. Bidusenko, Elena Yu. Schmidt, Igor A. Ushakov, Alexander V. Vashchenko and Boris A. Trofimov*

*A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia, Email: boris_trofimovirioch.irk.ru

I. A. Bidusenko, E. Y. Schmidt, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov, Org. Lett., 2021, 23, 4121-4126.

DOI: 10.1021/acs.orglett.1c01009 (free Supporting Information)


see article for more reactions

Abstract

N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in KOtBu/DMSO solution to provide 2,3,5-triarylpyrrolines in good yields. A subsequent in situ oxidation with chloranil or DDQ gives 2,3,5-triaryl-2H-pyrroles in good yields.

see article for more examples

proposed mechanism



Key Words

2H-pyrroles, chloranil


ID: J54-Y2021