An efficient method for the synthesis of 4-sulfenyl isoxazoles has been developed via AlCl-mediated electrophilic cyclization/sulfenylation of 2-alkyn-1-one O-methyloximes. Remarkably, N-arylsulfanylsuccinimides are employed as electrophiles for the construction of 4-arylsulfanyl isoxazoles, and 4-alkylsulfanyl isoxazoles are accessed with dialkyl disulfides as electrophiles.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.9b00256 | DOI Listing |
Chemistry
July 2024
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.
The regiodivergent synthesis of 4- and 5-sulfenyl oxazoles from 1,4,2-dioxazoles and alkynyl thioethers has been achieved. Gold-catalysed conditions are used to favour the formation of 5-sulfenyl oxazoles via β-selective attack of the nitrenoid relative to the sulfenyl group. In contrast, 4-sulfenyl oxazoles are formed by α-selective reaction under Brønsted acid conditions from the same substrates.
View Article and Find Full Text PDFJ Org Chem
April 2019
College of Chemistry, Chemical Engineering and Material Science , Shandong Normal University, Jinan 250014 , P. R. China.
An efficient method for the synthesis of 4-sulfenyl isoxazoles has been developed via AlCl-mediated electrophilic cyclization/sulfenylation of 2-alkyn-1-one O-methyloximes. Remarkably, N-arylsulfanylsuccinimides are employed as electrophiles for the construction of 4-arylsulfanyl isoxazoles, and 4-alkylsulfanyl isoxazoles are accessed with dialkyl disulfides as electrophiles.
View Article and Find Full Text PDFMol Vis
January 2018
Ocular Neovascular Disease Research Center, Inje University Busan Paik Hospital, Busan, Republic of Korea; Department of Ophthalmology, Inje University College of Medicine, Busan, Republic of Korea.
Purpose: We previously have reported that chondrocyte-derived extracellular matrix (CDECM) suppresses the growth of pterygium in athymic nude mice. The aim of this study is to demonstrate the effect of CDECM on the pterygium epithelial cells and molecular signaling pathways in human primary pterygium epithelial cells (hPECs).
Methods: Human conjunctival epithelial cells (hConECs) were used for identification of the effect of CDECM on normal conjunctiva.
4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones (4) were designed on the basis of biological isosterism and prepared in four steps. Some of these compounds showed sufficient pre-emergent herbicidal activities against various kinds of weeds. Among the synthesized compounds, 2-(N-(4-chlorophenyl)-N-isopropylcarbamoyl)-4-ethylthio-5-methyl-4 -isoxazolin-3-one (4cd) exhibited the most promising activity.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!