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Brønsted Acid Catalyzed Cyclization of Aminodiazoesters with Aldehydes to 3-Carboxylate-N-Heterocycles

Yang Jiao, Anrong Chen, Bangkui Yu and Hanmin Huang*

*Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. China, Email: hanminustc.edu.cn

Y. Jiao, A. Chen, B. Yu, H. Huang, Org. Lett., 2020, 22, 6031-6034.

DOI: 10.1021/acs.orglett.0c02125


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Abstract

A Brønsted acid catalyzed cyclization of aminodiazoesters with aldehydes provides a wide range of 5 to 7-membered 3-carboxylate-N-heterocycles. This reaction offers broad substrate scope and functional group compatibility.

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Details

The document describes a study on the Brønsted acid-catalyzed cyclization of aminodiazoesters with aldehydes to synthesize 3-carboxylate-N-heterocycles. This reaction is significant due to its broad substrate generality and functional group compatibility, producing a variety of 5-7 membered N-heterocycles. These heterocycles are valuable in synthetic and medicinal chemistry, serving as building blocks for bioactive molecules. The study highlights the use of PhCOOH as an effective catalyst, achieving high yields in methanol. The reaction mechanism involves the formation of an iminium ion, which facilitates cyclization and nitrogen extrusion. The synthesized products can undergo further transformations, demonstrating their utility in creating complex structures like nucleoside derivatives and Tiagabine. The research emphasizes the development of more general and straightforward synthetic methods for these compounds, addressing the limited scope of existing methods. The study also explores the scalability of the reaction, indicating its potential for preparing fine chemicals. Overall, this work provides a direct and efficient approach to synthesizing 3-carboxylate-N-heterocycles under mild conditions, with significant implications for synthetic chemistry.


Key Words

2-pyrrolines


ID: J54-Y2020