Palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines

Li Sun; Jiyu Li; Yafei Wu; Ying Li; Junqi Chen; Xiaoye Xia; Chunhao Yuan; Hongchao Guo; Biming Mao

doi:10.1039/D3OB01361H

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Palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines†

Li Sun,‡^a Jiyu Li,‡^a Yafei Wu,^a Ying Li,^a Junqi Chen,^a Xiaoye Xia,^a Chunhao Yuan,

^c Hongchao Guo

*^b and Biming Mao

*^a

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. China
E-mail: maobiming@sdfmu.edu.cn

^b Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
E-mail: hchguo@cau.edu.cn

^c School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University, Shandong Academy of Medical Sciences, Taian 271016, Shandong, P. R. China

Abstract

A palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines has been successfully developed under mild reaction conditions, affording pharmacologically interesting oxazine or hydropyrimidine derivatives in high yields (up to 99% yield). Furthermore, the cycloaddition reactions could be efficiently scaled up and several synthetic transformations were accomplished for the construction of other useful 1,3-oxazine and hydropyrimidinone derivatives.

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DOI: https://doi.org/10.1039/D3OB01361H
Article type: Communication
Submitted: 25 Aug 2023
Accepted: 27 Sep 2023
First published: 28 Sep 2023

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Org. Biomol. Chem., 2023,21, 8107-8111

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Palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines

L. Sun, J. Li, Y. Wu, Y. Li, J. Chen, X. Xia, C. Yuan, H. Guo and B. Mao, Org. Biomol. Chem., 2023, 21, 8107 DOI: 10.1039/D3OB01361H

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Organic & Biomolecular Chemistry

Palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines†

Abstract

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Palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines

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