pph3 -促进的磺胺-迈克尔加成驱动环化：获得螺酮衍生物的不同途径。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-16 DOI:10.1021/acs.joc.5c01450

Jyoti Chauhan,Jyoti Sikarwar,Rama Krishna Peddinti

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引用次数: 0

摘要

以3h -苯并[c][1,2]二硫醇-3-酮为硫代物，建立了一种新的三苯基膦介导的磺胺- michael加成触发级联反应，用于高效合成螺代氯罗曼酮衍生物。这种转化开始于还原S-S键的裂解，在温和的条件下平稳地传递各种螺-1,3-二甲基巴比妥-硫代罗曼酮和螺-1,3-茚二酮-硫代罗曼酮。目前的合成路线具有关键优势，包括操作简单，可扩展性和出色的官能团兼容性，以及跨基板的良好转换。此外，该方案避免了分离螺环加合物的柱层析等纯化技术，使其成为构建复杂含硫螺环支架的有价值的策略。

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PPh3-Promoted Sulfa-Michael Addition-Driven Cyclization: A Divergent Route to Access Spirothiochromanone Derivatives.

A novel triphenylphosphine-mediated sulfa-Michael addition-triggered cascade reaction has been developed for the efficient synthesis of spirothiochromanone derivatives using 3H-benzo[c][1,2]dithiol-3-one as a sulfur surrogate. This transformation initiates with reductive S-S bond cleavage, smoothly delivering a diverse array of spiro-1,3-dimethylbarbiturate-thiochromanones and spiro-1,3-indanedione-thiochromanones under mild conditions. The current synthetic route features key advantages including operational simplicity, scalability, and excellent functional group compatibility with good to excellent conversions across substrates. Furthermore, this protocol obviates purification techniques such as column chromatography for the isolation of spiro-adducts, making it a valuable strategy for the construction of complex sulfur-containing spirocyclic scaffolds.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.