Publications and Research

Document Type

Article

Publication Date

2020

Abstract

A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Brønsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Brønsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.

Comments

This is the accepted manuscript of an article published as: Domaradzki,Maciej E., Xiaochen Liu, Jiye Ong, Gyeongah Yu, Gan Zhang, Ariel Simantov, Eliyahu Perl, and Yu Chen. "Triflic Acid Mediated Sequential Cyclization of ortho- Alkynylarylesters with Ammonium Acetate." Tetrahedron, 2020, doi: https://doi.org/10.1016/j.tet.2020.131437

Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Available for download on Wednesday, August 03, 2022

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