Selective synthesis of 2-substituted 4-carboxy oxazoles, thiazoles and thiazolidines from serine or cysteine amino acids

(2-Deoxy-2-{[2-(2-pyridinyl-κN)-4-thiazolecarbonyl-κN3]amino}-α-d-glucopyranose)dichloropalladium(II) Methanol Solvate

“…Glycoconjugated 2-(2-pyridyl)thiazole ligand 1 was synthesized by the condensation of 2-(2-pyridinyl)-4-thiazolecarboxylic acid [7] with glucosamine in the presence of 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide (EDC) and 1-hydroxybenzotriazole (HOBT). Then, the reaction of 1 with sodium tetrachloropalladate(II) (Na 2 PdCl 4 ) in a mixed MeOH/H 2 O solvent afforded the desired glycoconjugated palladium(II) complex 2 in an 86% yield (Scheme 1).…”

Single‐Step Microwave‐Mediated Synthesis of Oxazoles and Thiazoles from 3‐Oxetanone: A Synthetic and Computational Study

“…Literature routes that build thiazoles with this 2,4-disubstitution pattern include Hantzsch syntheses [18] (thioamide condensations with pyruvate-type electrophiles), and thiazoline oxidation [19] or bromination/dehydrobromination [20] procedures. There were no trends between substituent character and reaction yield; the main factor determining the yield was the ease of separation of heteroarene product from unreacted amide or thioamide.…”

“…There were no trends between substituent character and reaction yield; the main factor determining the yield was the ease of separation of heteroarene product from unreacted amide or thioamide. Literature routes that build thiazoles with this 2,4-disubstitution pattern include Hantzsch syntheses [18] (thioamide condensations with pyruvate-type electrophiles), and thiazoline oxidation [19] or bromination/dehydrobromination [20] procedures. Our procedure is extremely competitive because of its directness and high atom-efficiency.…”

“…1 H, 19 F and 13 C NMR spectra were recorded using the deuterated solvent as the lock and the residual solvent as the internal reference. 1 H, 19 F and 13 C NMR spectra were recorded using the deuterated solvent as the lock and the residual solvent as the internal reference.…”

“…General: NMR spectra were recorded on Bruker DPX-400 or Avance DRX-500 spectrometers. 1 H, 19 F and 13 C NMR spectra were recorded using the deuterated solvent as the lock and the residual solvent as the internal reference. The multiplicities of the spectroscopic data are presented in the following manner: s = singlet, bs = broad singlet, d = doublet, dd = double doublet, ddd = doublet of double doublets, dt = doublet of triplets, qd = quartet of doublets, t = triplet, tt = triplet of triplets and m = multiplet.…”