Triflic Acid Mediated Sequential Cyclization of ortho-Alkynylarylesters with Ammonium Acetate

Authors

Maciej E. Domaradzki, CUNY Queens College
Xiaochen Liu, CUNY Queens College
Jiye Ong, CUNY Queens College
Gyeongah Yu, CUNY Queens College
Gan Zhang, CUNY Graduate Center
Ariel Simantov, CUNY Queens College
Eliyahu Perl, CUNY Queens College
Yu Chen, CUNY Queens CollegeFollow

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

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