We report a simple synthetic method for obtaining 3-hydroxy-4,5-disubstituted isothiazoles utilizing dithioester and aryl acetonitrile. The isothiazoles obtained in this method involve the formation of new C-C, C-O, and N-S bonds in one step using a simple base such as KOH under aerial conditions. The 3-hydroxy-4,5-disubstituted isothiazole was successfully employed for further functionalization. The strategy provides high selectivity for the synthesis of isothiazoles, which may have applications in pharmaceuticals, organic materials, and agrochemicals in both academic and industrial settings.
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http://dx.doi.org/10.1021/acs.joc.4c01222 | DOI Listing |
Org Biomol Chem
December 2024
Kangwon National University, Chun Cheon 24341, Korea.
-(tetra-aryl) picket calix[4]pyrrole 1 featuring -fluorophenyl groups at all four -positions in a -configuration has been synthesized and characterized unambiguously using single-crystal X-ray diffraction analysis. This pre-organized system possesses a deep binding pocket created by the four aryl groups so that anions can be accommodated through anion-π interactions and four-point N-H⋯anion hydrogen bonds. Single-crystal X-ray diffraction analysis of the CsF and TEAF (TEA = tetraethylammonium) complexes of receptor 1 unequivocally confirms the formation of 1 : 1 complexes, revealing the binding modes in the solid state.
View Article and Find Full Text PDFHarnessing the unique optical properties of chirality-enriched single-walled carbon nanotubes (SWCNTs) is the key to unlocking the application of SWCNTs in photonics. Recently, it has been discovered that chemical modification of SWCNTs greatly increases their potential in this context. Despite the dynamic progress in this area, the mechanism of the chemical modification of SWCNTs and the impact of the reaction conditions on the properties of the obtained functional nanomaterials remain unclear.
View Article and Find Full Text PDFJ Org Chem
November 2024
State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, People's Republic of China.
A facile and convenient metal-free direct oxidative amination of acetonitrile followed by cyclization with aroyl hydrazide for synthesizing oxadiazoles has been investigated. Disubstituted 1,3,4-oxadiazoles were obtained at 50-82% yields using readily available acetonitrile as both reagent and solvent. In addition, the reaction of aroyl hydrazides with thioacetamide and cyanothioacetamide afforded 5-methyl-2-aryl-1,3,4-thiadiazoles and 2-aryl-1,3,4-oxadiazole-2-acetonitriles as the main products, respectively.
View Article and Find Full Text PDFChemistry
December 2024
Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, 91400, Orsay, France.
J Org Chem
October 2024
Laboratory of Organic Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece.
A highly efficient, formed CuCl/TMEDA catalytic system (TMEDA = ,,','-tetramethylethylene-diamine) for the cross-coupling reaction of aryl acetonitriles with benzyl alcohols is reported. This user-friendly protocol, employing a low catalyst loading and a catalytic amount of base, leads to the synthesis of α-alkylated nitriles in up to 99% yield. Experimental mechanistic investigations reveal that the key step of this transformation is the C(sp)-H functionalization of the alcohol, taking place a hydrogen atom abstraction, with the simultaneous formation of copper-hydride species.
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