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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol200231zDOI Listing

Publication Analysis

Top Keywords

thioamide dianions
8
intramolecular cyclization
4
cyclization situ
4
situ generated
4
generated adducts
4
adducts formed
4
formed thioamide
4
dianions thioformamides
4
thioformamides leading
4
leading generation
4

Similar Publications

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 PDF

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 PDF

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 PDF

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 PDF

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.

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!