Category: 5053-24-7

Otsuka, Shinya published the artcilePalladium-Catalyzed Insertion of Isocyanides into the C-S Bonds of Heteroaryl Sulfides, Category: thiazole, the publication is Angewandte Chemie, International Edition (2018), 57(22), 6653-6657, database is CAplus and MEDLINE.

Insertion of tert-Bu isocyanide into the C(sp²)-S bonds of heteroaryl sulfides is catalyzed by a palladium diphosphine complex. Thioimidates generated through this reaction could be readily hydrolyzed under acidic conditions to yield the corresponding thioesters, which are of synthetic use. This insertion is useful because starting heteroaryl sulfides were readily prepared by either conventional ways or through sulfur-specific extended Pummerer reactions.

Angewandte Chemie, International Edition published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Arisawa, Mieko published the artcileRhodium-catalyzed 2-methylthiolation reaction of thiazoles/oxazoles using 2-(methylthio)thiazole, Application of 2-(Methylthio)thiazole, the publication is Heterocycles (2015), 90(2), 939-949, database is CAplus.

RhH(PPh₃)₄ and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles I (R¹ = Me, Ph, pMeOC₆H₄, etc.; R² = H, Me, n-C₄H₉, etc; X = O, S) using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium and various 2-methylthiolated thiazoles and oxazoles II were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.

Heterocycles published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Application of 2-(Methylthio)thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Evans, David L. published the artcileNickel peroxide dehydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocycles, Synthetic Route of 5053-24-7, the publication is Journal of Organic Chemistry (1979), 44(4), 497-501, database is CAplus.

Twenty-seven partially reduced O-, S-, and N-containing heterocycles were oxidized by NiO₂. Of particular interest were the conversions of several oxazolines to the corresponding oxazoles, a conversion apparently without precedent in the chem. literature, and the efficient oxidation of thiazolines to thiazoles. Since NiO₂ can effect thiazoline dehydrogenations in the presence of other functionalities, as may be judged by the successful oxidation of phleomycin A₂ to bleomycin A₂, the oxidant should be of utility for the preparation of natural products containing thiazoles.

Journal of Organic Chemistry published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Vernin, Gaston published the artcileThin-layer and gas chromatography of thiazole and benzothiazole heterocycles, Synthetic Route of 5053-24-7, the publication is Bulletin de la Societe Chimique de France (1967), 846-56, database is CAplus.

Compounds of the general formula I, II, and III were prepared according to known methods and the effect of different factors on their mobility was studied. The following were prepared (I, R, R1, R2, and b.p. given): H, H, H, 117-18°; Me, H, H, 128-30°; Et, H, H, 148°; H, Me, Me, 133°; H, Et, H, 145°; H, iso-Pr, H, 171°; H, H, Me, 141°; H, H, Et, 162°; Me, Me, H, 145°; Me, H, Me, 149°; H, Me, Me, 158°; iso-Pr, H, H, 160°; Pr, H, H, 175°; iso-Bu, H, H, 172°; tert-Bu, H, H, 180°; neopentyl, H, H, 198°; Cl, H, H, 142°; Br, H, H, b20 69-71°; iso-Pr, Me, H, b50 92°; tert-Bu, Me, H, b50 96°; Me, tert-Bu, H, b50 96°; Et, tert-Bu, H, b50 108°; iso-Pr, tert-Bu, H, b50 113°; tert-Bu, tert-Bu, H, b50 114°; MeS, H, H, -; EtS, H, H, -; PrS, H, H, -; iso-PrS, H, H, -; tert-BuS, H, H, -; iso-Bu, H, H, -; PhCH2S, H, H, -; SH, H, H, -; SH, Me, H, -; SH, H, Me, -; MeS, H, H, -, SH, Me, Me, -; MeS, Me, H, -; MeS, Me, Me, -; SH, Ph, H, -; (II, R, R1, and R2 given): H, H, H; H, Me, H; H, H, Me; Me, H, H; H, Me, Me; Me, Me, H; Me, Me, Me; H, Ph, H; and (III, R and b.p. given): H, 231°; Me, 240°; Et, 252°; Pr, 256°; iso-Pr, 261°; iso-Bu, 269°; tert-Bu, b16 138°; neopentyl, -, m. 52°. Thin-layer chromatog. gives a better separation than gas phase chromatog. for the 2-Me, 2-Ph, 4-Me, 4-Ph, and 2,4-di-Me compounds The mobility of methylthiazoles decreases in the following manner: 4-Me > 5-Me > 2-Me; polar effects are similar for the groups: Et, iso-Pr, and tert-Bu. Steric effects become important for the groups iso-Pr and tert-Bu.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C15H14Cl2S2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Chanon, Michel published the artcileUltraviolet, infrared, and nuclear magnetic resonance study of 4-thiazoline-2-thiones and of their 2-alkylthiothiazole isomers. The protomeric problem, COA of Formula: C4H5NS2, the publication is Bulletin de la Societe Chimique de France (1968), 2868-80, database is CAplus.

The uv spectra of the title materials were analyzed for protomeric thiol-thione in mols. in the neutral state, solvent effect, and proton fixation. The N.M.R. spectra showed a thiol-thione equilibrium, the effect of substituents, and the presence of ionized mols. The spectral characteristics in various ir regions were examined for use in the protomeric study. The advantages and disadvantages of each method used were assessed.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, COA of Formula: C4H5NS2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Evans, David L. published the artcileNickel peroxide dehydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocycles, Synthetic Route of 5053-24-7, the publication is Journal of Organic Chemistry (1979), 44(4), 497-501, database is CAplus.

Twenty-seven partially reduced O-, S-, and N-containing heterocycles were oxidized by NiO₂. Of particular interest were the conversions of several oxazolines to the corresponding oxazoles, a conversion apparently without precedent in the chem. literature, and the efficient oxidation of thiazolines to thiazoles. Since NiO₂ can effect thiazoline dehydrogenations in the presence of other functionalities, as may be judged by the successful oxidation of phleomycin A₂ to bleomycin A₂, the oxidant should be of utility for the preparation of natural products containing thiazoles.

Journal of Organic Chemistry published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Chanon, Michel published the artcileUltraviolet, infrared, and nuclear magnetic resonance study of 4-thiazoline-2-thiones and of their 2-alkylthiothiazole isomers. The protomeric problem, COA of Formula: C4H5NS2, the publication is Bulletin de la Societe Chimique de France (1968), 2868-80, database is CAplus.

The uv spectra of the title materials were analyzed for protomeric thiol-thione in mols. in the neutral state, solvent effect, and proton fixation. The N.M.R. spectra showed a thiol-thione equilibrium, the effect of substituents, and the presence of ionized mols. The spectral characteristics in various ir regions were examined for use in the protomeric study. The advantages and disadvantages of each method used were assessed.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, COA of Formula: C4H5NS2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Vernin, Gaston published the artcileThin-layer and gas chromatography of thiazole and benzothiazole heterocycles, Synthetic Route of 5053-24-7, the publication is Bulletin de la Societe Chimique de France (1967), 846-56, database is CAplus.

Compounds of the general formula I, II, and III were prepared according to known methods and the effect of different factors on their mobility was studied. The following were prepared (I, R, R1, R2, and b.p. given): H, H, H, 117-18°; Me, H, H, 128-30°; Et, H, H, 148°; H, Me, Me, 133°; H, Et, H, 145°; H, iso-Pr, H, 171°; H, H, Me, 141°; H, H, Et, 162°; Me, Me, H, 145°; Me, H, Me, 149°; H, Me, Me, 158°; iso-Pr, H, H, 160°; Pr, H, H, 175°; iso-Bu, H, H, 172°; tert-Bu, H, H, 180°; neopentyl, H, H, 198°; Cl, H, H, 142°; Br, H, H, b20 69-71°; iso-Pr, Me, H, b50 92°; tert-Bu, Me, H, b50 96°; Me, tert-Bu, H, b50 96°; Et, tert-Bu, H, b50 108°; iso-Pr, tert-Bu, H, b50 113°; tert-Bu, tert-Bu, H, b50 114°; MeS, H, H, -; EtS, H, H, -; PrS, H, H, -; iso-PrS, H, H, -; tert-BuS, H, H, -; iso-Bu, H, H, -; PhCH2S, H, H, -; SH, H, H, -; SH, Me, H, -; SH, H, Me, -; MeS, H, H, -, SH, Me, Me, -; MeS, Me, H, -; MeS, Me, Me, -; SH, Ph, H, -; (II, R, R1, and R2 given): H, H, H; H, Me, H; H, H, Me; Me, H, H; H, Me, Me; Me, Me, H; Me, Me, Me; H, Ph, H; and (III, R and b.p. given): H, 231°; Me, 240°; Et, 252°; Pr, 256°; iso-Pr, 261°; iso-Bu, 269°; tert-Bu, b16 138°; neopentyl, -, m. 52°. Thin-layer chromatog. gives a better separation than gas phase chromatog. for the 2-Me, 2-Ph, 4-Me, 4-Ph, and 2,4-di-Me compounds The mobility of methylthiazoles decreases in the following manner: 4-Me > 5-Me > 2-Me; polar effects are similar for the groups: Et, iso-Pr, and tert-Bu. Steric effects become important for the groups iso-Pr and tert-Bu.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C15H14Cl2S2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Frey, Lisa F. published the artcilePractical synthesis of a highly functionalized thiazole ketone, Name: 2-(Methylthio)thiazole, the publication is Tetrahedron (2003), 59(33), 6363-6373, database is CAplus.

5-(Ketoaryl)thiazole is a uniquely substituted ketone prepared via addition of a thiazole anion to an aromatic nitrile in good overall yield. An exploration into the generality of the addition of thiazole anions to nitriles allowed us to make a variety of thiazole ketones in good to excellent yields. The non-odorous thiolate-mediated demethylation reaction used in the synthesis of 5-(ketoaryl)thiazole is also presented.

Tetrahedron published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Name: 2-(Methylthio)thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Tang, Kuei C. published the artcileTunable heteroaromatic azoline thioethers (HATs) for cysteine profiling, Application In Synthesis of 5053-24-7, the publication is Chemical Science (2022), 13(3), 763-774, database is CAplus and MEDLINE.

Here we report a new series of hydrolytically stable chemotype heteroaromatic azoline thioethers (HATs) to achieve highly selective, rapid, and efficient covalent labeling of cysteine under physiol. conditions. Although the resulting cysteine-azoline conjugate is stable, we highlight traceless decoupling of the conjugate to afford unmodified starting components in response to reducing conditions. We demonstrated that HAT probes reverse the reactivity of nucleophilic cysteine to electrophilic dehydroalanine (Dha) under mild basic conditions. We demonstrated the umpolung capability of HAT probes for the modification of cysteine on peptides and proteins with various nucleophiles. We demonstrated that HAT probes increase the mass sensitivity of the modified peptides and proteins by 100 fold as compared to the classical methods. Finally, we extended the application of HAT probes for specific modification of cysteines in a complex cell lysate mixture

Chemical Science published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C6H3FN2, Application In Synthesis of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica