Category: 1826-13-7

Transition-Metal-Free ipso-Arylative Condensation was written by Sinclair, Geoffrey S.;Kukor, Andrew J.;Imperial, Kevin Karl G.;Schipper, Derek J.. And the article was included in Macromolecules (Washington, DC, United States) in 2020.Category: thiazole This article mentions the following:

The development of economical synthetic methods remains an important step toward the widespread use of conjugated polymers. Most well-established methods require either prefunctionalization with organometallic reagents or the use of expensive transition-metal catalysts. We have shown that 2-hydroxyalkyl- and 2-hydroxyaryl-substituted thiazole N-oxides can proceed through an ipso-arylative condensation that yields bithiazole-containing conjugated small mols. and polymers. The use of 2-hydroxyaryl substituents enables access to a wide scope of thiazole N-oxide substrates and presents an economical route to the synthesis of bithiazole-based conjugated polymers with varying phys. and electronic properties. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Absorption spectra of isomeric methyl- and phenylthiazoles and their simple and quaternary salts was written by Kornilov, M. Yu.;Aych, E. D.;Smeshko, L. I.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1973.Recommanded Product: 5-Phenylthiazole This article mentions the following:

The π-π* absorption maximum for the 2-, 4-, and 5-Me and the 2-, 4-, and 5-phenylthiazoles, their HCl salts, and the N-Me quaternary salts was determined Formation of the salt resulted in a 6-7 nm bathochromic shift for each of the methylthiazoles. The bathochromic shift was larger for 5-phenylthiazole and the quaternary salt of 4-phenylthiazole. The shifts were hypsochromic with 2-phenylthiazole. These changes are discussed in terms of steric hindrance and resonance. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Recommanded Product: 5-Phenylthiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Radical reactivity in thiazoles. III. Synthesis of aryl thiazoles and their derivatives. An analytical study was written by Varnin, G.;Aune, J. P.;Dou, H. J. M.;Metzger, J.. And the article was included in Bulletin de la Societe Chimique de France in 1967.Name: 5-Phenylthiazole This article mentions the following:

Aryl- and arylalkylthiazoles were prepared and their uv, ir, and N.M.R. spectra determined Thus, according to the method of Gabriel, thioamides were prepared by treating 0.1 mole of an amide in dioxane with 1.5/5 mole P2S5 45 min. at 40°. Formation of the resultant thioamides was followed by thin layer chromatog. using silica GF-254 and C6H6 containing 5% EtOH. The obtained thioamide was treated with 0.1 mole of the carbonyl derivative at 60°, and the reaction mixture kept 2 hrs. at 100° and acidified, and dioxane was steam distilled The resulting reaction product was neutralized and steam distilled to give the corresponding thiazole. Higher yields of thiazoles were obtained by using absolute EtOH in the presence of fused NaOAc and drops of piperidine. The α-bromoketones were prepared by treating the corresponding ketones with Br2 at 50-5° in aqueous solution in the presence of KClO4 as described by Catch and D. F. Elliot. Bromination may be also carried by the use of NaOBr, or N-bromosuccinimide. The thiazoles (I) prepared are listed in the table. The prepared thiazoles were analyzed by gas chromatog. using 10% silicone SE 30 on 60/80 mesh fire brick. The retention volume for I were given at 200° and were compared with those obtained on 5% carbowax 20 M on chromosorb P 60/80 mesh. [TABLE OMITTED] The Rf and Rm values for I were given using silica DF-5 and (1:1) C6H6-CH2Cl2 eluant mixture or Al2O3 DF-5 and 55:15 heptane-CH2Cl2 eluant mixture thin layer chromatog. The conditions were given. The uv, ir, and N.M.R. spectra were discussed. 65 references. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Name: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: 5-Phenylthiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Effect of primary amines of binuclear, noncondensed ring compounds on the growth of tubercle bacilli was written by Erlenmeyer, H.;Becker, C.;Sorkin, E.;Bloch, H.;Suter, E.. And the article was included in Helvetica Chimica Acta in 1947.Formula: C9H7NS This article mentions the following:

C.A. 41, 6925h. A systematic series of compounds similar in structure to p-H₂NC₆H₄Ph (I), with a tertiary C atom para to the NH₂ group, was prepared to test the influence of the tertiary linkage on tuberculostatic activity. The growth of tubercle bacillus in surface cultures on Lockemann medium is totally inhibited by 1-25 × 10^-7 M I. In comparison with 2 × 10^-4 M Na salicylate, I is 1600 times as effective in restricting the growth of tubercle bacillus in vitro, i.e., I has a salicylate number (SN) 1600. The selected compounds, 2-(p-aminophenyl)thiazole (II), 4-(p-aminophenyl)thiazole (III), 5-(p-aminophenyl)thiazole (IV), and the isoteric 3-(p-aminophenyl)pyridine (V), show total inhibition of Lockemann surface cultures at 2.5 × 10^-7, 5 × 10^-7, 1 × 10^-7, and 3.3 × 10^-7 M, resp., and have 800, 400, 2000, and 600 SN. The linkage relationship existing in I and the 3 thiazoles was demonstrated in the syntheses. The nitration of the corresponding phenylthiazoles with HNO₃ and H₂SO₄ at 0° gave the p-NO₂ derivative exclusively whereas nitration of BzOH yields only the m-NO₂ compound PhCSNH₂ (60 g.) and 50 g. dipolymerized BrCH₂CHO in 180 cc. absolute alc. containing 3 drops of piperidine were refluxed 10 hrs. The alc.-free reaction mixture was steam-distilled in the presence of 2 N Na₂CO₃ and the distillate was extracted with ether. Distillation of the oil from the evaporated dried extract yielded 47 g. (72%) 2-phenylthiazole, b₁₈ 125-8°, nitrated to give 80% of the corresponding 2-(p-nitrophenyl)thiazole, m. 147-8°. Reduction with Raney Ni in absolute alc. produced 2.75 g. (75%) II, m. 123-4°; Ac derivative, C₁₁H₁₀N₂OS, m. 140-1°; Bz derivative, C₁₆H₁₂N₂OS, m. 164-6°. The reduction of II gave orange crystals of 4,4′-di-2-thiazolylazoxybenzene, C₁₈H₁₂N₄OS₂, m. 234-5°. Nitration of 4-phenylthiazole produced 90% of needles of 4-(p-nitrophenyl)thiazole (VI), m. 177-8°, reduced to 83% III, m. 99-100°. As proof of structure, VI was degraded by oxidation with K₂Cr₂O₇ in H₂SO₄ to p-NO₂C₆H₄CO₂H in 62% yields. Bromination of 20 g. PhCH₂CHO in 100 cc. absolute CHCl₃ under CO₂ with 10 cc. Br 6 hrs. gave 32 g. of light-green oily PhCHBrCHO, converted according to Ger. pat. 670,131 (C.A. 33, 2909.5) with HCONH₂ and PS₅ in toluene to 14.5% 5-phenylthiazole (VII), m. 40-1°. Nitration of 2.5 g. VII gave 2.95 g. (92%) of crude nitration product, recrystallized from alc. to yellow needles of 5-(p-nitrophenyl)thiazole (VIII), C₉H₆N₂O₂S, m. 145-6°, oxidatively degraded to p-NO₂C₆H₄CO₂H. Catalytic reduction of 3.2 g. VIII with Raney Ni and recrystallization from H₂O produced 2.2 g. (80%) of colorless needles of IV, C₉H₈N₂S, m. 149.5-50.0°; BzO derivative m. 206°. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Formula: C9H7NS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

1,3-Dipolar cycloaddition reactions of thiazolium and benzothiazolium nitrogen ylides with acetylenic dipolarophiles was written by Chen, Teng Yueh;Liu, Jong Ho;Chen, Kong Ming. And the article was included in Proceedings of the National Science Council, Republic of China, Part A: Physical Science and Engineering in 1989.Recommanded Product: 1826-13-7 This article mentions the following:

Reaction of equimolar amounts of thiazolium and benzothiazolium N ylides with acetylenic dipolarophiles readily gave 1:1 cycloadducts dihydropyrrolo[2,1-b]thiazoles and -benzothiazoles. However, most of them dehydrogenated easily to fully aromatized pyrrolo[2,1-b]thiazoles and pyrrolobenzothiazole. Dihydroazepino[2,1-b]benzothiazole 1:2 cycloadducts were obtained from benzothiazolium N ylide I (R = Ph) and MeO₂CC:CCO₂Me (II). I (R = OEt) did not form the expected 1:1 cycloadducts with II. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Recommanded Product: 1826-13-7

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Nickel-Catalyzed C-H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules was written by Yamamoto, Takuya;Muto, Kei;Komiyama, Masato;Canivet, Jerome;Yamaguchi, Jun-Ichiro;Itami, Ken-Ichiro. And the article was included in Chemistry – A European Journal in 2011.Category: thiazole This article mentions the following:

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. It has been established that Ni(OAc)₂/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)₂/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, a new protocol was discovered for the present coupling using Mg(OtBu)₂ as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodol. has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling was written by Liu, Chengwei;Ji, Chong-Lei;Zhou, Tongliang;Hong, Xin;Szostak, Michal. And the article was included in Angewandte Chemie, International Edition in 2021.SDS of cas: 1826-13-7 This article mentions the following:

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chem. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling [e.g., benzoxazole + benzoic acid → 2-phenylbenzoxazole (92%)]. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetalation of the copper-aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7SDS of cas: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 1826-13-7

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Carbon-13 NMR studies of variously substituted phenylthiazoles. Substituent effects, conformational study and prototropic tautomerism was written by Faure, Robert;Assaf, Abdelghani;Vincent, Emile Jean;Aune, Jean Pierre. And the article was included in Journal de Chimie Physique et de Physico-Chimie Biologique in 1978.Synthetic Route of C9H7NS This article mentions the following:

The ¹³C NMR of I (R = H, 2-Ph, 4-Ph, 5-Ph) was examined and the dihedral angle between the Ph and thiazole ring systems determined; comparison of other heterocyclic ring systems with I indicated that the perturbation observed on Ph substitution decreased with the increase in heteroatom electronegativity. Steric interactions were observed in 4,5-disubstituted phenylthiazoles and the substituent effects were nonadditive; additivity was observed in 2,4- and 2,5-disubstituted phenylthiazoles. The protonation of I and the tautomerization of II (R¹ = H, Ph; R² = NH₂, SH, OH) was also discussed. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Synthetic Route of C9H7NS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Some thiazoles and oxazoles was written by Bachstez, Marcel. And the article was included in Berichte der Deutschen Chemischen Gesellschaft in 1914.Reference of 1826-13-7 This article mentions the following:

Rüdenburg, C. A. 8, 686. From 2 g. each of BzNHCH₂CH(OEt)₂ and P₂S₅, heated on the H₂O bath till the foaming ceases, is obtained 0.3 g. 2-phenylthiazole (Hubacher, Ann. 269, 234) . 1 g. HCONHCH₂Bz (a), m. 81-2° (Pictet and Gams, C. A. 4, 3222, give 70-1°), heated 10 min. with 1.5 g. P₂S₅, gives 0.6 g. 5-phenylthiazole, iridescent leaflets, m. 45-6°; hydrochloride, hygroscopic needles, decompose by much H₂O or by warming; chloroplatinate, yellow precipitate, decompose 281-2°; chloroaurate, yellow-red rhombic plates, sinters 170°, m. 185°, decompose about 223°; chromate, ocher-yellow rodlets and needles from 10% HCl, m. 108-9° (decompose); picrate, light yellow needles, m. 138-9° (decompose). 5-Phenyloxazole, from (a) and PCl₅ after 10 min. on the H₂O bath, m. 41-2°; hydrochloride, hygroscopic; chloroaurate, long orange needles, m. 149-50°; chloroplatinate, long light yellow needles, does not decompose 275°. α-Acetaminopropiophenone (b), obtained in 0.8 g. yield from 1 g. BzCHMeNH₂.HCl in 15 cc. ice H₂O and 2 cc. Ac₂O, rhombic pyramids from C₆H₆, m. 90-1°; with 2 parts PCl₅ 10 min. on the H₂O bath it gives 2,4-dimethyl-5-phenyloxazole, m. 51-2°; hydrochloride, hygroscopic rodlets, slowly volatilizes in vacuo, decompose by H₂O; chromate, orange needles, m. 100-1° (foaming); chloroplatinate, long yellow-red needles with 2 H₂O, m. 240° (foaming); chloroaurate, short rodlets; picrate, felted needles, m. 171-2.5°. 2,4-Dimethyl-5-phenylthiazole, obtained in 50% yield from equal parts of (b) and P₂S₄ heated 10 min. to 140°, b₇₆₈ 270-1°; hydrochloride, hygroscopic rodlets, decompose by much H₂O; chloroplatinate, long yellow-red needles with 2 H₂O, sinters 235°, m. 239-40° (foaming); chloroaurate, needles; chromate, fleshred needles, m. 105-6°; picrate, felted needles, m. 155.5-6.5°. Benzaminoisobutyrophenone, from BzCMe₂NH₂.HCl and BzCl in NaOH, needles from 50% alc., m. 61°, does not react with PCl₅ alone or in POCl₃. ω-Ethyloxalylaminoacetophenone, BzCH₂NHCOCO₂Et, from BzCH₂NH₂.HCl in cold H₂O treated with NaHCO₃ and ClOCCO₂Et, striated prisms from H₂O, m. 96-7°; the yield was so small that its reaction with PCl₄ could not be tried out. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Reference of 1826-13-7

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Pd-Catalyzed Decarbonylative C-H Coupling of Azoles and Aromatic Esters was written by Matsushita, Kaoru;Takise, Ryosuke;Hisada, Tomoya;Suzuki, Shin;Isshiki, Ryota;Itami, Kenichiro;Muto, Kei;Yamaguchi, Junichiro. And the article was included in Chemistry – An Asian Journal in 2018.Electric Literature of C9H7NS This article mentions the following:

A decarbonylative C-H coupling of azoles and aromatic esters by palladium catalysis was described. Previously reported Ni-catalyzed C-H coupling of azoles and aromatic esters had a significant drawback regarding the substrate scope. Herein, palladium catalysis employed instead of nickel and resulted in a broader substrate scope in terms of azoles and aromatic esters. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Electric Literature of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C9H7NS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica