School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran.
J Org Chem. 2011 Dec 16;76(24):9975-82. doi: 10.1021/jo201506d. Epub 2011 Nov 17.
We have developed a solvent-dependent method for the synthesis of novel benzo-δ-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.
我们开发了一种溶剂依赖性方法，用于合成新型苯并-δ-砜骨架。在 DMF 中，使用一锅法和 DBU 催化的 2-羟基苯甲醛与多种（E）-2-苯乙烯磺酰氯的缩合反应，以高产率得到了各种苄基苯并[e][1,2]恶噻嗪-4(3H)-酮-2,2-二氧化物。另一方面，最初制备的 2-甲酰基苯基-（E）-2-苯乙烯磺酸盐衍生物在 MeOH 中经历 DBU 催化反应，以中等至良好的收率得到一系列 3-[甲氧基（苯基）甲基]苯并[e][1,2]恶噻嗪-2,2-二氧化物。这些反应可能分别通过 DBU 催化的 O-磺酰化/分子内 Baylis-Hillman/1,3-H 迁移或脱水串联序列进行。
