Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-24 DOI:10.1021/acs.orglett.4c04539

Palanisamy Soundarya, Sayan Pahan, Govindasamy Sekar

引用次数: 0

Abstract

Developing new types of molecular photoswitches with novel functionalities allows experts to advance their applications in biology, chemistry, and material sciences. Herein, we report an efficient synthetic protocol for the synthesis of thioindirubin derivatives from commercially available starting materials. This domino reaction proceeds through aldol condensation followed by intramolecular C–S bond formation and selective cyclization in a 5-exo-trig manner. Nuclear magnetic resonance studies suggest the ability to tune both isomerization directions upon irradiation with different ultraviolet and visible light (370–640 nm light-emitting diode). The newly reported hemithioindigo photoswitches have various applications in the areas of life science and material sciences.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.