Author: tianli

Synthesis of N-arylamines in dry media and their antibacterial activity was written by Ramana, M. M. V.;Sharma, Madhu R.. And the article was included in Journal of Chemical and Pharmaceutical Research in 2013.Reference of 1843-21-6 This article mentions the following:

A number of N-aryl amines were synthesized by N-arylation of primary/secondary amines with activated aryl halides in the presence of KF/Al₂O₃ (basic) dry media at room temperature The newly prepared Compounds were examined for their antibacterial activity against E. coli, S. typhi, B. subtilis, and S. aureus. Some of the compounds showed significant antibacterial activity. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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 1843-21-6

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

Cross-coupling of sulfonic acid derivatives via aryl-radical transfer (ART) using TTMSS or photoredox was written by Nacsa, Eric D.;Lambert, Tristan H.. And the article was included in Organic Chemistry Frontiers in 2018.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

The intramol. cross-coupling of sulfonic acid derivatives occurs in the presence of tris(trimethylsilyl)silane (TTMSS) at room temperature and in air to form biaryl compounds A photoredox-catalyzed procedure is also described. These protocols provide mild and convenient alternatives to standard tin-mediated reactions. Combined with the trivial preparation of the substrates from activated sulfonic acids and 2-halophenols or anilines, this work presents a useful means to employ sulfonic acid derivatives in cross-coupling transformations. A modified linker to realize high regioselectivity is also presented. Finally, a one-pot cross-coupling procedure is demonstrated. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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 is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Electric Literature of C6H7ClN2O3S2

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

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas was written by Shibasaki, Kaho;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2019.Category: thiazole This article mentions the following:

Treatment of alkylarenes with N-bromosuccinimide in a mixture of Et acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of di-Et carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino-4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, resp., in one pot [e.g., ethylbenzene + thiourea → 2-amino-4-phenylthiazole (84%)]. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Category: thiazole).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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.Category: thiazole

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

Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed versus Copper-Catalyzed Aminations of Halothiazoles was written by Toulot, Stephanie;Heinrich, Timo;Leroux, Frederic R.. And the article was included in Advanced Synthesis & Catalysis in 2013.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles, e.g., I, were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key mols. in pharmaceutical research. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine

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

Dipole moments of phenylthiazoles was written by Bonnier, Jane M.;Arnaud, Roger. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1970.Synthetic Route of C9H7NS This article mentions the following:

Dipole moments of I (where R, R1, and (or) R2 = H or Ph) were measured in in CCl4 or cyclohexane at 20° and calculated by the LCAO method. The dipole moments in CCl4 and cyclohexane were very similar and did not indicate the formation of complexes between I and CCl4. The calculated values were satisfactory, except for I (R = R1 = R2 = Ph). 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. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Synthetic Route of C9H7NS

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

Oxidation of aromatic thiocarbamides. Tetraphenyl formamidine monosulfide hydrobromide was written by Suresh, K. S.. And the article was included in Journal of the Indian Chemical Society in 1960.Application of 1843-21-6 This article mentions the following:

Br (6 ml. in 100 ml. 50% EtOH) was added to 16 g. thiocarbanilide (I) in 160 ml. alc. and kept 1.5 hr. at 60° and S was filtered off. The mixture was kept overnight and filtered to give 6-8 g. PhHNC(:NPh)SC(:NPh)NHPh.HBr (II), m. 156°; picrate m. 118°. II with boiling H₂O gave PhHNC(:NPh)NHPh (III); III and NH₃ gave phenylthiourea (IV). II with NH₃ gave III and IV. II with boiling acidified EtOH gave carbanilide (V) and I; the filtrate and NH₃ gave IV. II with p-toluidine (150-60°, 15 min.) gave N-phenyl-N’-(p-tolyl)thiourea. III and V were also obtained. Addition of Br (in EtOH) to II (in alc. with HBr) gave, on basification, a thiadiazole (VI), m. 136°. Br solution (17 ml.) (1 ml. Br in 20 ml. CHCl₃) was added to 5 g. II in 50 ml. CHCl₃ to give 6 g. of solid (VII), C₂₆H₂₃N₄Br₄S (sic), containing 3 active Br. VII with Na bisulfite gave VI, C₂₆H₂₀N₄S.HBr. VI with Br gave a solid, m. 85-95°. II (2 g.) with 3 ml. SOCl₂ gave a solid (VIII), m. 100-30°, and (from the filtrate) 2-phenylaminobenzothiazole. VIII kept with H₂O overnight gave VI. VIII with Na bisulfite gave II. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application of 1843-21-6

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

Pyrolyses of 2-aminobenzazoles was written by Martineau, Andre;DeJongh, Don C.. And the article was included in Journal of Analytical and Applied Pyrolysis in 1983.Category: thiazole This article mentions the following:

The pyrolysis and mass spectral fragmentation of I (R = Ph, H; X = O, NH, S) follow similar paths and mechanisms. The replacement of H in I (R = H) by Ph allowed the observation of reaction intermediates, in both the pyrolysis and the mass spectra, which were too unstable for direct observation with I (R = H); the Ph group behaved as an internal trapping group. The M⁺ and (M – H)⁺ peaks are the most intense mass spectral peaks for I. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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

Nucleophilic reactivity of 2-chlorobenzothiazole was written by Todesco, Paolo Edgardo;Vivarelli, Piero. And the article was included in Gazzetta Chimica Italiana in 1962.Category: thiazole This article mentions the following:

The reaction of MeONa with 5- or 6-substituted derivatives of 2-chlorobenzothiazole has been studied. 2-Chlorobenzothiazole (I), b₂₁ 133-4°, was prepared according to Moon (CA 43, 6670c). The 6-nitro derivative (II) of I, pale yellow needles, m. 191-2°, was prepared by nitrating I with KNO₃ and H₂SO₄ (U.S. 2,659,730, CA 49, 2519a; Katz, CA 46, 3044b). The 5-nitro derivative (III) of I, m. 112°, was prepared by adding an excess of SO₂Cl₂, in the cold, to 0.003 mole of 2-mercapto-5-nitrobenzothiazole, crude m. 223-5°, prepared in turn in 60% yield, by adding a KSH solution (0.01 mole KOH in little water and 30 ml. alc., saturated with H₂S) to a boiling alc. solution of 2-bromo-5-nitroaniline, cooling, adding 0.3 ml. CS₂, stirring 4 hrs. at 80°, steam distilling, cooling, making ammoniacal, filtering off S, and precipitating the product by making acid with HCl. The 4-nitro derivative (IV) of I, yellow needles, m. 169-70°, was prepared by diazotizing 2-amino-4-nitrobenzothiazole (Erlenmeyer and Ueberwasser, CA 34, 2844⁶), m. 254°, and decomposing the diazonium salt with cold Cu₂Cl₂-HCl. The 6-methyl derivative (V) of I, m. 49-50°, resulted from 2-amino-6-methylbenzothiazole, m. 135-6°, according to Metzger and Plank (CA 50, 15512a). The 5-methyl derivative (VI) of I, m. 41-2° (cold pentane) was made by treating 2-mercapto-4-methylbenzothiazole with SO₂Cl₂, the intermediate being prepd, according to Teppema and Sebrell (CA 21, 2688). The 6-chloro derivative (VII) of I, m. 98-9°, was prepared by diazotizing 2-amino-6-chlorobenzothiazole, m. 200°, in a mixture of HCO₂H, AcOH, and HCl, and decomposing the diazo salt with Cu₂Cl₂-HCl (Stuckwisch, CA 44, 2514a). The intermediate was obtained according to Kaufmann and Kuchler (CA 28, 5066⁶). The 5-chloro derivative (VIII) of I, m. 70-1°, was prepared by treating 2-mercapto-5-chlorobenzothiazole, m. 196-7°, with SO₂Cl₂. The 6-methoxy derivative (IX) of I, m. 53-4°, was prepared according to Stuckwisch (loc. cit.). For the reaction with Me-ONa, MeOH solutions of the reagents, previously brought to reaction temperature, were mixed and kept at const, temperature, taking samples at intervals and pouring them into an excess of aqueous HNO₃, followed by AgNO₃, and determining Cl^– by the Volhard method. The resulting data were plotted and used to calculate the rate constant and energy of activation of the reactions. The second-order rate const, k (10³ sec.^-1 mole^–1) for 0°, 13°, 25°, 35°, and 45°, followed by the activation energy E (kcal. mole^-1) for the various derivatives of I: I, -, -, 0.55, 1.43, 3.39, 16.9; IV, -, 42.8, 132.0, 335.0, -, 16.3; III, 8.09, -, 87.8, 205.0, -, 15.4; VIII,-, 2.53, 6.37, 15.20, -, 15.8; VI, -, 0.116, 0.374, 1.05, -, 17.8; II, -, 97.0, 280.0, 647.0, -, 14.2; VII, -, 1.01, 3.25, 7.79, -, 16.0; V, -, 0.057, 0.197, 0.578, -, 18.3; and IX, -, 0.0244, 0.0893, 0.255, -, 18.7. Electron-attracting substituents (Cl, NO₂) speed up the reaction, while electron-donor substituents (Me, MeO) slow it down. The log k of the reaction gave a straight line function of Hammett’s σ (of. Jaffe, Chem. Rev. 53, 191(1953)), except in the case of II. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Category: thiazole).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Category: thiazole

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

Facile synthesis of the new tripodal tetraamine ligand tris(thiazolylmethyl) amine, and full characterization of two ferrous complexes was written by Thibon, Aurore;Karmazin-Brelot, Lydia;Mandon, Dominique. And the article was included in Dalton Transactions in 2013.Quality Control of Thiazol-2-ylmethanamine This article mentions the following:

The authors report the facile synthesis of the new tris(thiazolylmethyl)amine, TTA ligand (3) and the full characterization in solution and in the solid state of two ferrous complexes, [(TTA)FeCl₂] (1) and [(TTA)Fe(OTf)₂] (2). TTA, the first example of a simple tris(thiazolemethyl)amine chelate – the second one only within this class of tripods – exerts a weak ligand field and the tertiary amine is weakly bound to the metal center. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Quality Control of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Quality Control of Thiazol-2-ylmethanamine

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

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan was written by Lv, Fengping;Li, Zhi-fang;Hu, Wenhao;Wu, Xiaohua. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Category: thiazole This article mentions the following:

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biol. processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chem. stimuli, the authors developed a cell-based high-throughput screening (HTS) platform for searching chem. enhancers of FOG of α-DG from a large chem. library with 364,168 compounds Sequential validation of the hits from a primary screening campaign and chem. works led to identification of a cluster of compounds that pos. modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Category: thiazole).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Category: thiazole

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