Category: 5053-24-7

Liang, Xinyu published the artcileThe Aryl Sulfide Synthesis via Sulfide Transfer, COA of Formula: C4H5NS2, the publication is Chemistry – A European Journal (2022), 28(35), e202200869, database is CAplus and MEDLINE.

Aryl sulfides are in great demands in drugs and materials sciences. To avoid using nucleophilic and noxious thiols, many efforts have been focused on exploring novel sulfide resources. Herein, a reductive Pd-catalyzed, Ni-mediated method to synthesize aryl sulfides via a sulfide transfer reaction is developed. The utility and scope of this reaction is exemplified by various aryl electrophiles and aryl sulfides. Mechanistic studies reveal two competing catalytic cycles of sulfide transfer and aryl transfer in this reaction, where the former one is favored over the later one because of the large energy barrier difference during the transmetalation. Moreover, two important chems. are late-stage functionalized by this method, exhibiting the potential applications in drugs and materials science.

Chemistry – A European Journal 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

Batty, J. W. published the artcileAcetylene reactions. III. Reaction of aminobutynes with carbon disulfide, HPLC of Formula: 5053-24-7, the publication is Journal of the Chemical Society (1949), 786-9, database is CAplus.

Addition of 10 cc. CS₂ to 11.1 g. iso-PrNHCHMeCCH (I), 4 g. NaOH, and 30 cc. H₂O at 50°, with stirring for an addnl. 2 hrs., gives 58% 4-methyl-3-isopropyl-5-methylene-2-thiazolidinethione (II), MeCH.C(:CH₂).S.CS.NCHMe₂, b_0.4 130-5°, m. 43°. II results in 8-g. yield on refluxing 4 hrs. 10.6 g. I and 10 cc. CS₂ in 50 cc. EtOH. II with O₃ gives HCHO. BuNHCHMeCCH (12.5 g.) yields 87% of the 3-Bu homolog of II, b_0.5, 140-2°, n_D¹⁶ 1.5975. 3-Cyclohexyl analog of II, b_0.15 150-60°, m. 69-70°. 3-Benzyl analog, pale yellow, b_0.075 165-75°. (iso-PrNHCHMeCC)₂ (5 g.) yields 2.5 g. 1,2-bis(4-methyl-3-isopropyl-2-thiono-5-thiazolyl)ethane, [S.CS.N(CHMe₂).CMe:CCH₂]₂, m. 270° (decomposition). Solution of 2.5 g. II in cold concentrated H₂SO₄ gives 2 g. 4,5-dimethyl-3-isopropyl-2(3H)-thiazolethione (III), m. 84-6°; III results in 7.2-g. yield from 9 g. MeCHBrAc with 4.85 g. CS₂ and 7.5 g. iso-PrNH₂ in 25 cc. EtOH. 3-Bu homolog of III, pale yellow, m. 42-4°; cyclohexyl analog (IV), m. 104°; benzyl analog, m. 111°. CS₂ (19.5 g.) and 30 g. iso-PrNH₂ in 100 cc. EtOH, treated (0.5 hr.) with ClCH₂Ac, give 26 g. 4-methyl-3-isopropyl-2(3H)-thiazolethione, m. 68-9°; 13 g. 2-ClCH₂CH₂Ac gives 21 g. 10-3-ketobutyl isopropyldithiocarbamate, m. 62°; this is not cyclized by treatment with cold concentrated H₂SO₄ or on heating in EtOH. 2-Cyclohexylamino-3-butyne (20 g.), on hydrogenation in MeOH over Raney Ni, gives 15 g. N-cyclohexyl-sec-butylamine (V), b₂₅ 86-8°, n_D¹⁶ 1.4350 (HCl salt, m. 210°); 10 g. V, 9 g. MeI, and 5 g. KOH, heated 2 hrs. on the steam bath and the base in dilute HCl treated with a slight excess of saturated aqueous NaNO₂, give 4.5 g. N-cyclohexylmethyl-sec-butylamine (VI), b₂₂ 90-3° (methiodide, m. 174-6°); 3 g. IV and 20 cc. Raney Ni in 80 cc. EtOH, refluxed 4 hrs., give 0.4 g. VI. MeNHCH₂CH₂OH (5 g.) in 7 cc. CS₂, heated 3.5 hrs. at 120-40°, gives 5.8 g. 3-methyl-2-thiazolidinethione, b. 90-100 °/10^-4 mm. (bath), m. 68-9°; with MeI it yields 2-(methylmercapto) thiazoline-MeI, m. 132°. BuNHCH₂CH₂OH (5 g.) and 5 cc. CS₂, heated 3.5 hrs. at 120-40°, give 4.9 g. 3-butyl-2-thiazolidinethione, yellow, b. 90-5°/10^-4 mm. (bath), n_D^22.5 1.5970.

Journal of the Chemical Society 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, HPLC of Formula: 5053-24-7.

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

Nuhn, P. published the artcileGlycosides of heterocycles. XXX. Glucosides of imidazole-, oxazole-, and thiazole-2-thiones, Synthetic Route of 5053-24-7, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1968), 301(3), 186-200, database is CAplus and MEDLINE.

(cf. CA 68:39990b; 40021t. The reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide (I) with thiazole-2-thiones carried out by the Sabalitschka method (CA 23:3239), i.e. under SN2 conditions, gave exclusively 1-thio-D-glucosides. Similar results were obtained with oxazole-2-thiones and imidazole-2-thiones. Under SN1 conditions the formation of 1-thio-D-glucosides was favored only when the heterocyclic ring bore bulky substituents at position 4, otherwise the formation of glycosytamines was preferred. 2-Thmzolethione (II) (0.01 mole) and 0.56 g. KOH in 5 ml. H2O was mixed with 4.1 g. I in 15 ml. Me2CO, agitated until the mixture turned neutral and worked-up to give 65% 2-(tetra-O-acetyl-β-D- glucopyranosylthio)thiazole (IIIa) (Q = tetra-O-acetyl-β-D-glucopyranosyl throughout this abstract), m. 119-22° (MeOH), [α]22D -10.7° (c 5, CHCl3). IIIb, m. 107-8° (50% MeOH), [α]22D -11.7° (c5, CHCl3), and IIIc, m. 151-3° (MeOH), [α]22D -31.7° (c5, CHCl3), were similarly prepared Deacetylation with MeONa afforded the free glucosides: 2-(β-D-glucopyranosylthio)-4-methylthiazole (IIId) (G = β-D-glucopyranosyl throughout this abstract), m. 152-5°, [α]22D -66.8° (c 2, H2O), and IIIe, m. 87-90° (H2O), [α]22D -62.9° (c 2, H2O). Using the same procedure as for IIIa, 4-methyloxazole-2-thione (IV) afforded 4-methyl-2-(tetra-O-acetyl-β-D-glucopyranosylthio)oxazole (Va), m. 105-10°, [α]22D -17° (c 5, CHCl3). Vb, m. 160-3° (MeOH), [α]22D -22° (c 5, CHCl3), and Vc, m. 117-19° (MeOH), [α]22D -13.9° (c 5, CHCl3), were prepared similarly. Tetra-o-acetylglucosides, deacetylated as previously, yielded the free glucosides: Vd, m. 125-8°, [α]22D -49.5° (c 2, H2O); Ve, m. 137-40°,α]22D -63.2° (c 2, H2O); and Vf, m. 85-90°, [α]25D -54.5° (c 1.5, Me2CO). 1-Methylimidazole-2-thione (VI) reacted with I under the Sabalitschka method gave 55% of 1-methyl-2-(tetra-O-acetyi-1-β-D-glucopyranosylthio)imidazole (VII), m. 99-102° (70% EtOH), [α]22D 0° (CHCl3). II (0.01 mole) dissolved in 10 ml. H2O containing 0.56 g. KOH and the solution treated slowly with a solution of 2.72 g. HgCl2 and 2 g. NaCl in 40 ml. H2O yielded bis(2-thiazolythio)mercury (VIII), m. 182-90° (decomposition). VIII (0.005 mole) was dissolved in 30 ml. HCONMe2, the solution mixed with 30 ml. C6H6, the latter distilled and the remaining dry solution treated with 4.1 g. I, kept 14 hrs. at 50°, diluted with 200 ml. H2O, extracted 5 times with CHCl3, the combined extracts washed with 30% KI followed by 5% Na2CO2, dried and evaporated, gave 50% 3-(tetra-O-acetyl-1-β-D-glucopyranosyl)thiazole-2-thione (IXa), m. 179-82° (MeOH), [α]22D 68.3° (c 5, CHCl3). IXa deacetylated as previously, afforded IXb, m. 173-83°, [α]22D 35° (c 2, H2O). Similarly, bis(1-methylimidazol-2-ylthio)mercury, m. 220-5° (decomposition), produced 25% 1-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)imidazole-2-thione (X), m. 148-9° (MeOh), α]23D 36° (c 5, CHCl3). VI (0.02 mole), refluxed with 6 ml. (Me3Si)2NH for 8 hrs. gave 1-methyl-3-trimethylsilylimidazole-2-thione, b9 142-3°. This, heated for 2 hrs. with I at 120-30° in vacuo, diluted with 100 ml. CHCl3 and the solution washed with 5% Na2CO3 yielded 30% X. Similarly, 2-trimethylsilylthiothiazole, b. 143-5°, afforded IIIa, while 2-trimethylsilylthio-4-phenyloxazole, b9 147-51°, gave 72% Vb. 1-Thio-D-glucosides heated in toluene with HgBr2 were converted in high yield into glycosylamines. Thus, IIIa (2.5 millimoles) was refluxed 5 hrs. with 0.9 g. HgBr2 in 50 ml. of dry toluene, the solution washed with 30% KI followed by 5% Na2CO3, dried and evaporated to give 95% IXa. Likewise, VII produced 73% X, Va gave 20% 3-(tetra-O-acetyl-β-D-glucopyranosyl)-4-methyloxazole-2-thione (XIa), m. 163-6° (MeOH), [α]22D 73.8° (c 5, CHCl3), while Vc yielded 55% XIb, m. 143-5° (MeOH), [α]22D -47.4° (c 5, CHCl3). Deacetylation of XIb afforded XIc, m. 200-5°, [α]20D -3.5° (c2, HCONMe2). Transglycosylation of IIIb resulted in 25% IXc, m. 192-4°, [α]22D 66° (c 5, CHCl3). In the case of 4-Ph derivatives, no conversion into glycosylamines was observed. Instead, partial anomerization occurred: Vb yielded 5% of 2-(tetra-O-acetyl-α-D-glucopyranosylthio)-4-phenylthiazole, m. 102-6° (MeOH), [α]22D 156° (c 5, CHCl3), while IIIc gave 30% 2-(tetra-O-acetyl-α-D-glucopyranosylthio)-4-phenyloxazole, m. 138-40° (MeOH), [α]22D 228° (c 5, CHCl8), which on deacetylation afforded the free glucoside, an amorphous solid, [α]22D 226° (c 2, H2O). AcCH2OH (3 g.) dissolved in 40 ml. EtOH, treated with 5.8 g. KCNS and 3 ml. concentrated HCl and refluxed 24 hrs. gave 65% 4-methyloxazole-2-thione (XII), m. 149-52° (MeOH). II (2 g.), 5 g. Ag2O, and 15 g. MeI refluxed 8 hrs. gave 80% 2-methylthiothiazole, b26 59-62°. Similarly, XII yielded 2-(methylthio)-4-methyloxazole, b8 44-5°.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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 artcileApplications of Snyder’s theory on linear adsorption chromatography to heterocyclic compounds. I. Influence of the polar and steric effects of various substituents on the adsorption energy of thiazoles on alumina, Product Details of C4H5NS2, the publication is Journal of Chromatography (1970), 46(1), 48-65, database is CAplus.

The Snyder theory of linear adsorption chromatog., that was applied to on e hundred thiazole derivatives, made it possible to determine exptl. the adsorption energies of the compounds and to compare these with the adsorption energies calculated by means of fixed tables. In a study on thiazoles containing one or two alkyl groups, this comparison made it possible to determine the variations in adsorption energy of the N atom of the ring due to the polarization effects and to the steric effects induced by the alkyl groups and to relate these effects to the constant relations which exist between the polarization and steric effects of the substituents. A similar investigation was made on 4-aryl thiazoles with various substituents in the 2-position. In this case variations in the adsorption energy of the mols. due to the polarization effects of the groups substituted para to the phenyl group with respect to the substituents in the 2-position were studied, and the mutual electronic interactions between the various groups were determined

Journal of Chromatography 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 C12H23N3S, Product Details of C4H5NS2.

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

Iwasaki, Masayuki published the artcilePalladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides, Synthetic Route of 5053-24-7, the publication is Organic Letters (2016), 18(7), 1642-1645, database is CAplus and MEDLINE.

Palladium-catalyzed carbothiolation of terminal alkynes with azolyl sulfides affords various 2-(azolyl)alkenyl sulfides with perfect regio- and stereoselectivities. The present addition reaction proceeded through a direct cleavage of carbon-sulfur bonds in azolyl sulfides. The resulting adducts that are useful intermediates in organic synthesis are further transformed to multisubstituted olefins containing azolyl moieties.

Organic Letters 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

You, Jinmao published the artcileStudy of the retention behavior of eight thiazole derivatives by reversed-phase high performance liquid chromatography, Application In Synthesis of 5053-24-7, the publication is Fenxi Huaxue (1996), 24(4), 447-541, database is CAplus.

The capacity factors k’ of eight thiazole derivatives on reversed-phase ODS column with methanol/water as eluant were measured. The linear regression between the lnk’ values and methanol concentrations according to equation lnk’ = a + cC was carried out and a good linear relation was obtained. The parameters a and c with various concentrations of methanol as the eluant were measured. The effect of various salts and triethylamine on the capacity factors of thiazole derivatives were studied. A mobile phase of methanol:0.2 mol/L HOAc-NaOAc buffer solution (pH 4.0):triethylamine 45:54:1 and UV detection at 254 nm gave satisfactory results.

Fenxi Huaxue 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 C14H10N2O, Application In Synthesis of 5053-24-7.

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

Liu, Xiang-Wei published the artcileDiversified syntheses of multifunctionalized thiazole derivatives via regioselective and programmed C-H activation, Related Products of thiazole, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(22), 4599-4602, database is CAplus and MEDLINE.

The sequential construction of diversified multifunctionalized thiazole derivatives through Pd-catalyzed regioselective C-H alkenylation was accomplished. This versatile approach provides the diversified thiazole derivatives featuring orthogonal substitution patterns at the C-2, C-4 and C-5 positions from mono-substituted (2- or 4-substituted) thiazole derivatives or even more challenging simple thiazole.

Chemical Communications (Cambridge, United Kingdom) 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, Related Products of thiazole.

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

Dai, Wen published the artcileHighly Chemoselective and Enantioselective Catalytic Oxidation of Heteroaromatic Sulfides via High-Valent Manganese(IV)-Oxo Cation Radical Oxidizing Intermediates, HPLC of Formula: 5053-24-7, the publication is ACS Catalysis (2017), 7(7), 4890-4895, database is CAplus.

A manganese complex with a porphyrin-like ligand that catalyzes the highly chemoselective and enantioselective oxidation of heteroaromatic sulfides, including imidazole, benzimidazole, indole, pyridine, pyrimidine, pyrazine, sym-triazine, thiophene, thiazole, benzothiazole, and benzoxazole, with hydrogen peroxide is described, furnishing the corresponding sulfoxides in good to excellent yields and enantioselectivities (up to 90% yield and up to >99% ee) within a short reaction time (0.5 h). The practical utility of the method has been demonstrated in the gram-scale synthesis of chiral sulfoxide. Mechanistic studies, performed with ¹⁸O-labeled water (H₂¹⁸O), hydrogen peroxide (H₂¹⁸O₂), and cumyl hydroperoxide, reveal that a highvalent manganese-oxo species is generated as the oxygen atom delivering agent via carboxylic acid assisted heterolysis of O-O bonds. D. functional theory (DFT) calculations were also carried out to give further insight into the mechanism of manganese-catalyzed sulfoxidation On the basis of the theor. study, the coupled high-valent manganese(IV)-oxo cation radical species, which bears obvious similarities with that of reactive intermediates in the catalytic oxygenation reactions based on the cytochrome P 450 and metalloporphyrin models, has been proposed as the reactive oxidant in the non-heme manganese catalyst system.

ACS Catalysis 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, HPLC of Formula: 5053-24-7.

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

Li, Zijie published the artcileEfficient room temperature catalytic synthesis of alternating conjugated copolymers via C-S bond activation, Synthetic Route of 5053-24-7, the publication is Nature Communications (2022), 13(1), 144, database is CAplus and MEDLINE.

Structural defects in conjugated copolymers are severely detrimental to the optoelectronic properties and the performance of the resulting electronic devices fabricated from them. Therefore, the much-desired precision synthesis of conjugated copolymers with highly regular repeat units is important, but presents a significant challenge to synthetic materials chemists. To this end, aryl sulfides are naturally abundant substances and offer unrealized potential in cross-coupling reactions. Here we report an efficient room temperature polycondensation protocol which implements aryl disulfide C-S activation to produce defect-minimized semiconducting conjugated copolymers with broad scope and applicability. Thus, a broad series of arylstannanes and thioethers are employed via the present protocol to afford copolymers with number-average mol. weights (Mns) of 10.0-45.0 kDa. MALDI and NMR anal. of selected copolymers reveals minimal structural defects. Moreover, the polymer trap d. here is smaller and the field effect mobility higher than that in the analogous polymer synthesized through thermal-activation Stille coupling.

Nature Communications 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 artcileSynthesis and physicochemical study of sulfides, sulfoxides and sulfones in the thiazole series, Recommanded Product: 2-(Methylthio)thiazole, the publication is Journal of Heterocyclic Chemistry (1978), 15(8), 1361-6, database is CAplus.

The alkylation of Δ⁴-thiazoline-2-thiones under phase transfer catalysis conditions gave the corresponding thio ethers, e.g., I, in good yields. The oxidation of 2-alkylthiazoles with m-ClC₆H₄C(O)OOH gave the corresponding sulfoxides or sulfones depending on exptl. conditions in yields of âˆ?0-90%. IR, ¹H NMR mass spectra, and chromatog. data are reported for most of the compounds studied.

Journal of Heterocyclic 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 C4H6N2, Recommanded Product: 2-(Methylthio)thiazole.

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