Reactions of thioamide dianions, derived from secondary N-arylmethyl thioamides using BuLi, with thioformamides followed by the addition of iodine to yield 5-amino-2-thiazolines are described. Treatment of the 5-amino-2-thiazolines with iodine leads to a highly efficient production of 5-aminothiazoles. When N,N-diarylthioformamides are employed in this process, fluorescent 5-N,N-diarylthiazoles are obtained.
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RSC Adv
May 2022
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University Yanagido Gifu 501-1193 Japan
A series of 5--arylaminothiazoles were synthesized with facile diversity-oriented synthesis from readily available starting materials the reaction of thioamide dianions and thioformamides. The introduction of various substituents at the 2-position of a thiazole ring (, 2-pyridyl, 4-methylpyridyl, and phenyl groups) and on the nitrogen atom (, -tolyl and phenyl groups) significantly influenced the absorption and emission spectra of the isolated compounds. X-ray analysis confirmed that the substituents at the amino site were twisted from a thiazole ring, while the formation of its nickel complex showed dinuclear metal complexes bridged with chlorine atoms.
View Article and Find Full Text PDFInorg Chem
September 2021
Department of Chemistry, Boston University, Boston, Massachusetts 02215, United States.
A new template condensation reaction has been discovered in a mixture of Pt(II), thiobenzamide, and base. Four complexes of the general form [Pt(ctaPh)], R = CH (), H (), F ), Cl (), cta = ondensed hiomide, have been prepared under similar conditions and thoroughly characterized by H NMR and UV-vis-NIR spectroscopy, (spectro)electrochemistry, elemental analysis, and single-crystal X-ray diffraction. The ligand is redox active and can be reduced from the initial monoanion to a dianionic and then trianionic state.
View Article and Find Full Text PDFJ Org Chem
November 2015
Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan.
A series of 5-N-arylaminothiazoles was prepared by reacting thioamide dianions derived from secondary thioamides with thioformamides, followed by sequential oxidation with iodine. X-ray analyses demonstrated that they adopt structures that are highly twisted from planar conformations. Their orientations were tuned by the steric and/or electronic interactions of the substituents at their 2-, 4-, and 5-positions.
View Article and Find Full Text PDFChemistry
January 2013
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
Addition reactions of thioamide dianions that were derived from N-arylmethyl thioamides to imines and aziridines were carried out. The reactions of imines gave the addition products of N-thioacyl-1,2-diamines in a highly diastereoselective manner in good-to-excellent yields. The diastereomeric purity of these N-thioacyl-1,2-diamines could be enriched by simple recrystallization.
View Article and Find Full Text PDFOrg Lett
April 2011
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
Reactions of thioamide dianions, derived from secondary N-arylmethyl thioamides using BuLi, with thioformamides followed by the addition of iodine to yield 5-amino-2-thiazolines are described. Treatment of the 5-amino-2-thiazolines with iodine leads to a highly efficient production of 5-aminothiazoles. When N,N-diarylthioformamides are employed in this process, fluorescent 5-N,N-diarylthiazoles are obtained.
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