光催化芳构化驱动的非张力酮衍生螺-二氢喹唑啉酮的C-S和C-Se键构建

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-05-13 DOI:10.1021/acs.joc.5c00499

Tao Wang,Jin-Long Dai,Yi-Feng Jiang,Shenghu Yan,Jia-Yin Wang

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引用次数: 0

摘要

在可见光照射下，在碱的存在下，实现了螺-二氢喹唑啉酮与磺化试剂的解构功能化反应。该反应使非张力环体系能够直接开环，生产出骨架多样化的功能化喹唑啉酮，收率中等至较高。多种磺化试剂，包括二芳基二硫化物、硫代磺酸盐、二硫代磺酸盐和1-[（三氟甲基）硫]-2,5-吡咯烷二酮均可用于该转化。此外，二硒醚二芳基和硒代磺酸盐也可与螺-二氢喹唑啉酮偶联形成C-Se键。机理研究表明，该反应是通过自由基-自由基耦合途径进行的。

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Construction of C-S and C-Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones.

A novel and robust deconstructive functionalization reaction of spiro-dihydroquinazolinones with sulfenylating reagents in the presence of base has been realized under visible light irradiation. This reaction enabled the direct ring-opening of unstrained cyclic ring systems, producing skeletally diverse functionalized quinazolinones with moderate to good yields. A range variety of sulfenylating reagents including diaryl disulfide, thiosulfonate, dithiosulfonate and 1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione were compatible for this transformation. In addition, diaryl diselenide and selenosulfonate could also couple with spiro-dihydroquinazolinones to form C-Se Bonds. Mechanistic studies revealed that the reaction proceeds via a radical-radical coupling pathway.

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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.