碱基介导串联Michael加成和SuFEx环化合成含硫酮的螺菌吲哚

IF 4.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2025-09-28 DOI:10.1021/acsomega.5c05571

Kimberleigh B. Govender, , , Sandile B. Simelane, , , Lloyd C. Chetty, , , Hendrik G. Kruger, , , Thavendran Govender, , , Per I. Arvidsson*, , and , Tricia Naicker*,

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引用次数: 0

摘要

含硫的螺环吲哚因其重要的生物活性而被公认，但在螺环核心中获得这些具有不同杂原子的化合物仍然具有挑战性。本研究介绍了一种简单高效的碱介导串联Michael加成反应和SuFEx环化反应合成新型含硫酮的螺菌吲哚。该转化发生在绿色溶剂中，这对抑制副反应至关重要，从而成功合成了20种新型磺酮-螺酰吲哚和两种耐环化的磺酸盐。此外，还探索了该反应的手性变体，为未来对映选择性方法的发展奠定了基础。

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Base-Mediated Tandem Michael Addition and SuFEx Cyclization for the Synthesis of Sultone-Containing Spirooxindoles

Sulfur-containing spirooxindoles are recognized for their significant biological activity, yet accessing these compounds with diverse heteroatoms in the spirocyclic core has remained challenging. This study introduces a simple and efficient base-mediated tandem Michael addition reaction and SuFEx cyclization to synthesize novel sultone-containing spirooxindoles. The transformation occurred in a green solvent, which proved essential in suppressing side reactions, leading to the successful synthesis of 20 novel sultone-spirooxindoles and two sulfonates that are resistant to cyclization. Additionally, a chiral variant of the reaction was explored, laying the groundwork for the future development of enantioselective methods.

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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.