Department of Organic Chemistry, Faculty of Science and Informatics, Institute of Chemistry, University of Szeged, Dóm tér 8, 6720 Szeged, Hungary.
ELKH-SZTE, Stereochemistry Research Group, University of Szeged, Eötvös utca 6, 6720 Szeged, Hungary.
Molecules. 2022 Sep 2;27(17):5671. doi: 10.3390/molecules27175671.
-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst 15 is a convenient choice. By applying mechanochemical activation in the preparation of this -heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product.
杂环化合物，如喹唑酮衍生物，具有显著的生物活性。如今，随着对环境友好、可持续工艺的需求不断增加，使用可再生资源化合物、易于分离的多相催化剂和高效、替代的活化方法的应用变得尤为重要。在这项研究中，我们开发了一种方便、绿色的方法，通过蒽酰胺和乙酰丙酸乙酯的双重环缩合级联反应，制备 3a-甲基-2,3,3a,4-四氢吡咯并[1,2-]喹唑啉-1,5-二酮。筛选了各种多相 Brønsted 酸催化剂，结果表明 Amberlyst 15 是一种方便的选择。通过在制备这种杂三环化合物时首次应用机械化学活化，与传统条件下需要 24 小时相比，所需时间缩短至 3 小时，即可获得目标产物的高产率。
