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Iodine-Promoted Oxidative Cyclization of Acylated and Alkylated Derivatives from Epoxides toward the Synthesis of Aza Heterocycles

Alageswaran Jayaram, Karthick Govindan, Vijaya Raghavan Kannan, Vijay Thavasianandam Seenivasan, Nian-Qi Chen and Wei-Yu Lin*

*Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC, Email: wylinkmu.edu.tw

A. Jayaram, K. Govindan, V. R Kannan, V. T. Seenivasan, N.-Q. Chen, W.-Y. Lin, J. Org. Chem., 2023, 88, 1749-1761.

DOI: 10.1021/acs.joc.2c02802


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Abstract

A ring-opening reaction of epoxides with 2-aminobenzamide in the presence of I2/DMSO provides acylated and alkylated quinazoline derivatives. The developed mild and efficient protocol tolerates a broad range of functional group. The application of continuous flow techniques allows for faster reaction time and higher yields.

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Key Words

quinazolinones


ID: J42-Y2023