Bischler-Napieralski Synthesis of Polycyclic N-Heteroaromatics Based on TfO-Promoted Electrophilic Activation of -Aryl-2-Propynamides.

J Org Chem

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

Published: March 2022

2-Propynamides have been never used as substrates in classic and TfO-promoted Bischler-Napieralski reactions. In this article, a novel tandem synthesis of benzo[]acridines is developed from -aryl-2-propynamides and alkynes consisting of a TfO-promoted intermolecular Bischler-Napieralski reaction and a TfOH-promoted intramolecular Friedel-Crafts reaction.

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http://dx.doi.org/10.1021/acs.joc.1c02918DOI Listing

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