A concise synthesis of thioaurones NBS-induced cyclization of MOM-protected 2'-mercaptochalcones.

Org Biomol Chem

School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.

Published: February 2023

A mild and efficient approach for the synthesis of thioaurones NBS-induced cyclization of methoxymethyl-protected mercapto-chalcones has been developed. This simple method is highly functional group tolerant and provides straightforward access to thioaurones in good to high yields.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d2ob01995gDOI Listing

Publication Analysis

Top Keywords

synthesis thioaurones
8
thioaurones nbs-induced
8
nbs-induced cyclization
8
concise synthesis
4
cyclization mom-protected
4
mom-protected 2'-mercaptochalcones
4
2'-mercaptochalcones mild
4
mild efficient
4
efficient approach
4
approach synthesis
4

Similar Publications

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues.

Molecules

June 2024

Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Viale delle Scienze, Ed. 17, I-90128 Palermo, Italy.

Aurones, particular polyphenolic compounds belonging to the class of minor flavonoids and overlooked for a long time, have gained significative attention in medicinal chemistry in recent years. Indeed, considering their unique and outstanding biological properties, they stand out as an intriguing reservoir of new potential lead compounds in the drug discovery context. Nevertheless, several physicochemical, pharmacokinetic, and pharmacodynamic (P3) issues hinder their progression in more advanced phases of the drug discovery pipeline, making lead optimization campaigns necessary.

View Article and Find Full Text PDF

Thioaurone chromophores, part of the indigoid family and commonly named hemithioindigos, have recently gained attention due to their interesting photoswitching properties. The study focuses on heterocyclic hemithioindigos (Het-HTIs) and investigates their synthesis using electron-rich and electron-poor heterocycles and modifications to the thioindigo moiety. Furthermore, it aims to evaluate the photoswitching performances of these synthesised compounds, with a particular emphasis on the influence of the heterocycles on the photoisomerization capabilities, which was found to be more prominent than the modifications made to the thioindigo moiety.

View Article and Find Full Text PDF

A concise synthesis of thioaurones NBS-induced cyclization of MOM-protected 2'-mercaptochalcones.

Org Biomol Chem

February 2023

School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.

A mild and efficient approach for the synthesis of thioaurones NBS-induced cyclization of methoxymethyl-protected mercapto-chalcones has been developed. This simple method is highly functional group tolerant and provides straightforward access to thioaurones in good to high yields.

View Article and Find Full Text PDF

An efficient method for synthesizing thioaurones has been developed using xanthate as an odorless sulfur surrogate. This reaction's key success lies in the use of iodine as a reagent, which promotes the α-iodination followed by cyclization of saturated ketones. This methodology has also been demonstrated with less reactive 2'-bromochalcones in good yield.

View Article and Find Full Text PDF

Synthesis of Benzothiophene-Fused Oxa[6.6.5]tricyclic Skeletons through a Cinchonidine- or NaOH-Promoted Quadruple Domino Sequence.

Chemistry

July 2019

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin, 300384, P.R. China.

Two base-promoted quadruple domino reactions between thioaurones and allylic phosphonium salts have been developed to synthesize benzothiophene-fused oxa[6.6.5]tricyclic skeletons in moderate to good yields with excellent stereoselectivity and broad functional-group tolerance.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!