Departments of Biochemistry and Radiation Oncology, The University of Texas Southwestern Medical Center at Dallas, Dallas, Texas 75390, United States.
Department of Chemistry, Indian Institute of Technology Gandhinagar, Palaj, Simkheda, Gandhinagar, Gujarat 382355, India.
J Org Chem. 2022 Jan 7;87(1):125-136. doi: 10.1021/acs.joc.1c02036. Epub 2021 Dec 28.
Quinazolin-dione--3-alklyl derivatives are the core scaffolds for several categories of bioactive small molecules, but current synthetic methods are costly, involve environmental hazards, and are not uniformly scalable. Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione--3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from isatin that take advantage of capture of imidic acid under acidic conditions. We further show that this method can be used for the synthesis of a wide variety of derivatives with medicinal uses.
喹唑啉-4,3-二酮-3-烷基衍生物是几类生物活性小分子的核心骨架，但目前的合成方法成本高、存在环境危害，且不具有普遍的可扩展性。在这里，我们报告了一种从靛红出发，一锅法合成取代的喹唑啉-4,3-二酮-3-烷基（异吲哚-8-仲酰胺（IASAs）的异构体）的廉价、灵活和可扩展的方法，该方法利用了在酸性条件下亚氨基甲酸的捕获。我们进一步表明，该方法可用于合成具有药用价值的各种衍生物。
