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DABCO 催化的 - 未取代靛红、- 环亚甲胺叶立德 1,3-二极体与 Morita-Baylis-Hillman 碳酸酯的单-/二烯丙基化反应。

DABCO-Catalyzed Mono-/Diallylation of -Unsubstituted Isatin ,'-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates.

机构信息

College of Science, Sichuan Agricultural University, Ya'an 625014, China.

The Yingjing County Emergency Management Agency, Ya'an 625200, China.

出版信息

Molecules. 2023 Mar 28;28(7):3002. doi: 10.3390/molecules28073002.

Abstract

Allylation of -unsubstituted isatin ,'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature, rapidly gave -allylated and , -diallylated isatin ,'-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.

摘要

在室温下,在 1-10mol%DABCO 的存在下,用 Morita-Baylis-Hillman 碳酸酯对 -未取代的靛红、-环亚甲胺进行烯丙基化反应,迅速以中等至高产率得到 -烯丙基化和,-二烯丙基化的靛红、-环亚甲胺 1,3-二极体。该反应具有温和的反应条件、易于实际操作和大多数情况下较短的反应时间。此外,通过与马来酰亚胺或 Knoevenagel 加合物的[3+2]或[3+3]-环加成,烷基化产物转化为新型双环螺吡咯烷氧吲哚衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10ce/10095907/2eb1c8eb27be/molecules-28-03002-g001.jpg

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