Day: January 5, 2023

Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts was written by Guan, Weiye;Liao, Jennie;Watson, Mary P.. And the article was included in Synthesis in 2018.Computed Properties of C4H6N2S This article mentions the following:

Cross-couplings of aralkyl pyridinium tetrafluoroborates and vinylboronic acids or esters was developed. Via aralkyl pyridinium intermediates, aralkyl amines were engaged in these cross-couplings through C-N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Computed Properties of C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Computed Properties of C4H6N2S

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

Direct amination of derivatives of benzothiazole was written by Vel’tman, R. P.. And the article was included in Zhurnal Obshchei Khimii in 1956.Application In Synthesis of Benzothiazole-5-carboxylic acid This article mentions the following:

Heating 6.4 g. 2-bromo-5-nitroaniline and 65 ml. 85% HCO₂H on steam bath 3 hrs. gave 89% 1-formylamino-2-bromo-5-nitrobenzene, m. 202-3° (from EtOH); with Na₂S₂ this gave 5-nitrobenzothiazole (cf. Fries and Wolter, C.A. 31, 1405¹). This reduced with SnCl₂-HCl to 5-aminobenzothiazole-H₂O, 60%, m. 76°. Oxidation of 5-methylbenzothiazole with KMnO₄ gave 5-carboxybenzothiazole, m. 261-2° (from H₂O); Et ester, m. 106-8° (from aqueous EtOH). The 5-substituted benzothiazoles were refluxed with equimolar amounts of NH₂OH.HCl and aqueous NaOH for 0.5-4 hrs. (the NO₂ derivative failed to react after a prolonged period). The usual treatment yielded the following products: 2-amino-5-methylbenzothiazole, m. 171-2°, 68%, from 5-methylbenzothiazole; 2,5-diaminobenzothiazole, m. 175°, 72%, from 5-aminobenzothiazole; 2-amino-5-carboxybenzothiazole, decompose 300°, 64%, from 5-carboxybenzothiazole. The 5-carbethoxy derivative failed to react as did the NO₂ derivative 2-Amino-5-benzothiazolecarboxylic acid gave the Et ester, m. 200-1°. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Application In Synthesis of Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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 In Synthesis of Benzothiazole-5-carboxylic acid

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

Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles was written by Motiwala, Hashim F.;Kumar, Raj;Chakraborti, Asit K.. And the article was included in Australian Journal of Chemistry in 2007.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines, e.g., I (R = H, Me, MeO, F, Cl, Br, OH, Ac, CO₂Me or NO₂), and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed Thus, the treatment of 4,7-dichloroquinoline (1 equivalent) with a mixture of aniline (2 equivalent) and phenol (2 equivalent) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equivalent) was sep. treated with 2-aminophenol (2 equivalent) and 4-aminophenol (2 equivalent), 4-(2′-hydroxyphenyl)-7-chloroquinoline and 4-(4′-hydroxyphenyl)-7-chloroquinoline, resp., were formed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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

Thiazoles. XI. The preparation of 2-amino-5-(phenylazo)thiazoles and the reductive scission of 2,2′-azothiazoles and 2-(phenylazo)thiazoles with phenylhydrazine was written by Beyer, Hans;Wolter, Gerhard. And the article was included in Chemische Berichte in 1952.Product Details of 6318-74-7 This article mentions the following:

A diazonium solution from 9.3 g. PhNH₂ buffered with AcONa added at 0° to 11.4 g. 2-amino-4-methylthiazole (I) gives 90.6% 2-amino-4-methyl-5-(phenylazo)thiazole (II), p-RC₆H₄N:N.C:CR’.N:C(NH₂).S (IIa, R = H, R’ = Me), orange needles, m. 184° (di-Ac derivative, prepared by heating 1.09 g. II with 3 cc. Ac₂O 1 h. on a water bath, fine yellow needles, m. 254-5°). 5-p-Tolylazo homolog (IIa, R = R’ = Me), 90.5%, long dark red columns from AcOEt-Me₂CO, m. 189-90°, or rhombic sepia leaflets from EtOH, m. 190-1° (di-Ac derivative, yellow needles, m. 251°); 5-p-nitrophenyl analog (IIa, R = NO₂, R’ = Me), 93.5%, fine dull red needles, m. 192° (di-Ac derivative, dark red leaflets, m. 206°). Coupling the diazonium compound from 17.2 g. p-H₂NC₆H₄SO₂NH₂ (III) with I gives 75% p-(2-amino-4-methyl-5-thiazolylazo)benzenesulfonamide (IIa R = SO₂NH₂, R’ = Me), m. 202° (di-Ac derivative, cubelike orange-yellow crystals, m. 223°). Coupling the diazonium salt from 9.3 g. PhNH₂ with 17.6 g. 2-amino-4-phenylthiazole gives 87.8% 2-amino-4-phenyl-5-(phenylazo)thiazole (IIa, R = H, R’ = Ph), fine felted cinnabar needles, m. 195° (di-Ac derivative, felted yellow needles, m. 214°); 5-p-tolylazo homolog (IIa, R = Me, R’ = Ph), 71.4%, fine felted red-orange needles, m. 200° (di-Ac derivative, long felted yellow needles, m. 217°); 5-p-nitrophenyl analog (IIa, R = NO₂, R’ = Ph), 90.8%, fine moss-green needles, m. 254° (Ac derivative, shiny dark green crystals, m. 293°); p-(2-amino-4-phenyl-5-thiazolylazo)benzenesulfonamide (IIa R = SO₂NH₂, R’ = Ph) 75%, bright red needles with a green surface sheen, m. 255° (di-Ac derivative, small cinnabar-red needles, m. 293°). Coupling the diazonium salt from 10.7 g. p-toluidine with 10 g. 2-aminothiazole (IV) gives 72% 2-amino-5-(p-tolylazo)thiazole (IIa, R = Me, R’ = H), small fine red needles, sintering 180°, m. 205° (di-Ac derivative, dark brown powder, m. 243°); coupling the diazonium salt from 17.2 g. III with 10 g. IV gives 75% p-(2-amino-5-thiazolylazo)benzene sulfonamide (IIa, R = SO₂NH₂, R’ = H), microcrystalline brown-yellow powder, m. 223° (di-Ac derivative, yellow-brown amorphous powder, m. 235°). Azothiazoles are reductively split by PhNHNH₂ to the corresponding NH₂ compounds Heating 3.7 g. di-Et 2,2′-azobis(4-methyl-5-thiazolecarboxylate) and 10.8 g. PhNHNH₂ (V) slowly to 180° and keeping the mixture 5 min. at 180° and overnight at 20° give 78% Et 2-amino-4-methyl-5-thiazolecarboxylate, needles, m. 175-6°. Similarly, Et 2-phenylazo-4-methyl-5-thiazolecarboxylate and V give 90% of the 2-phenylhydrazino analog, rhombic leaflets, m. 194°, which, on further heating with V at 200° gives 72% 2-amino analog; in the same way, 2-phenylazo-4,5-diphenylthiazole gives the 2-amino compound, m. 186°. Heating 2,2′-azobis(4-phenylthiazole) or 2-phenylazo-4-phenylthiazole with V at 180° gives the corresponding hydrazo compounds which, on further heating at 220°, give 18 and 14% 2-amino-4-phenylthiazole, m. 147°. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Product Details of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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.Product Details of 6318-74-7

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

Palladium-catalyzed arylation of azole compounds with aryl halides in the presence of alkali metal carbonates and the use of copper iodide in the reaction was written by Pivsa-Art, Sommai;Satoh, Tetsuya;Kawamura, Yoshiki;Miura, Masahiro;Nomura, Masakatsu. And the article was included in Bulletin of the Chemical Society of Japan in 1998.Related Products of 1826-13-7 This article mentions the following:

The reactions of iodobenzene with azole compounds, 1,2-disubstituted imidazoles and 2-substituted oxazoles and thiazoles, were examined in the presence of catalytic amounts of Pd(OAc)₂ and PPh₃ in DMF using alkali metal carbonates as bases. It was found that the coupling products, 5-arylazoles, e.g., I (Ar = Ph, 1-naphthyl, 2-thienyl, etc.), could be selectively produced in good yields by using Cs₂CO₃. In the case that their 2-position is unsubstituted, the site could also be arylated. In reactions using bromobenzene in place of iodobenzene, K₂CO₃ was also as effective as Cs₂CO₃. The addition of a stoichiometric amount of CuI appeared to specifically promote the reactions of thiazoles as well as those of thiophene derivatives The reactions of 2-unsubstituted azole compounds with aryl iodides could be mediated by CuI to some extent without using the palladium species to give 2-arylazoles. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Related Products of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 1826-13-7

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

Programmed synthesis of arylthiazoles through sequential C-H couplings was written by Tani, Satoshi;Uehara, Takahiro N.;Yamaguchi, Junichiro;Itami, Kenichiro. And the article was included in Chemical Science in 2014.Computed Properties of C9H7NS This article mentions the following:

A programmed synthesis of arylthiazoles (2-aryl, 4-aryl, 5-aryl, 2,4-diaryl, 2,5-diaryl, 4,5-diaryl, and 2,4,5-triaryl) via palladium or nickel catalyzed sequential C-H couplings of unfunctionalized thiazole using eleven distinct synthetic routes was discussed. This methodol. led to the synthesis of over 150 arylthiazoles including fatostatin (SREBP inhibitor). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Computed Properties of C9H7NS

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

Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase was written by Balti, Monaem;Plas, Aurelie;Meinguet, Celine;Haufroid, Marie;Themans, Quentin;Efrit, Mohamed Lotfi;Wouters, Johan;Lanners, Steve. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Quality Control of 2-Chloro-5-phenylthiazole This article mentions the following:

Docking studies of 4-phenylthiazolinethione on human IDO1 suggest complexation of the heme iron by the exocyclic sulfur atom further reinforced by hydrophobic interactions of the Ph ring within pocket A of the enzyme. On this basis, chem. modifications were proposed to increase inhibitory activity. Synthetic routes had to be adapted and optimized to yield the desired substituted 4- and 5-arylthiazolinethiones I (X = 2-OCH₃, 3-F, 4-CN, etc.) and II (X = H, 2-OCH₃, 3-Br, etc.). Their biol. evaluation shows that 5-aryl regioisomers are systematically less potent than the corresponding 4-aryl analogs. Substitution on the Ph ring does not significantly increase inhibition potency, except for 4-Br and 4-Cl derivatives In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Quality Control of 2-Chloro-5-phenylthiazole).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Quality Control of 2-Chloro-5-phenylthiazole

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

Synthesis and bio-activity evaluation of tetraphenyl(phenylamino) methylene bisphosphonates as antioxidant agents and as potent inhibitors of osteoclasts in vitro was written by Balakrishna, A.;Reddy, M. Veera Narayana;Rao, P. Visweswara;Kumar, M. Anil;Kumar, B. Siva;Nayak, S. K.;Reddy, C. Suresh. And the article was included in European Journal of Medicinal Chemistry in 2011.Quality Control of 2-Methylthiazol-5-amine This article mentions the following:

A new series of tetra-Ph bisphosphonates have been elegantly synthesized by one-pot method and were characterized by elemental anal., FTIR, ¹H, ¹³C, ³¹P NMR, mass spectra and evaluated for their in vitro anti-bone resorptive activity by inhibiting growth of osteoclasts. Two bisphosphonates showed marked inhibition ratio (8 μM and 10 μM) and emerged as lead compounds All compounds were tested for their antioxidant (DPPH scavenging, reducing power and inhibition of lipid peroxidation). They exhibited potent in vitro antioxidant activity dose-dependently. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Quality Control of 2-Methylthiazol-5-amine).

2-Methylthiazol-5-amine (cas: 89281-44-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Quality Control of 2-Methylthiazol-5-amine

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

Investigation of abiotic degradation of tire cryogrinds was written by Thomas, Jomin;Moosavian, Seyed Kasra;Cutright, Teresa;Pugh, Coleen;Soucek, Mark D.. And the article was included in Polymer Degradation and Stability in 2022.Related Products of 1843-21-6 This article mentions the following:

The abundance of microplastics found in the environment is a major cause of concern. Tire tread particles containing additives such as curing accelerators and antioxidants, can be a major source of elastomer pollution in the environment. Such tire particles combined with road pavement particles are referred to as tire and road wear particles, TRWP. The environmental availability from parent elastomers and the release of additives in the process of abiotic degradation were evaluated using freeze-thaw, wet-dry and accelerated UV-weathering experiments Acceleration factor determination tests were conducted to correlate UV-exposure to the natural aging in the environment. Freeze-thaw testing showed many additives such as di-Ph guanidine (DPG), benzothiazole sulfenamide (BTS) and para-phenylene diamine (6 PPD) as THF leachates and BTS transformation products. Further, UV exposure equivalent to 1.5 yr., 3 yr. and 5 yr. aging resulted in the formation a combination of ketones and carboxylic acids for styrene butadiene rubber (SBR), natural rubber (NR), and butadiene rubber-based tire cryogrinds. Attenuated total reflectance- Fourier- transform IR spectroscopy (ATR-FTIR) was used to detect the degradation of the elastomers on UV-exposure while gas chromatog.-mass spectroscopy (GC-MS) was used as a nontargeted, suspect screening anal. technique. The degradation intermediates and leachates identified using GC-MS represents useful data for the life cycle anal. of the functional polymers and additives and their possibility of environmental release. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Related Products of 1843-21-6).

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. 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.Related Products of 1843-21-6

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

Renal cystic disease induced by diphenylthiazole was written by Gardner, Kenneth D. Jr.;Evan, Andrew P.. And the article was included in Kidney International in 1983.Electric Literature of C15H12N2S This article mentions the following:

Intranephron hydrostatic pressures were monitored while microperfusing proximal nephrons in diphenylthiazole (DPT)-exposed rat kidneys. Intranephron hydrostatic pressures rose with microperfusion and did so at lower rates of perfusion among DPT exposed nephrons, as compared to normal kidneys. Subsequent light and electron microscopic examination of DPT-exposed kidneys showed micropolyps partially occluding inner medullary and intrapapillary collecting ducts. DPT-induced renal cystic disease resembles other forms of chem. induced renal cystic disease in its functional and structural parameters except that micropolyp formation appears to occur nearer the papillary tip. Conditions in the DPT-exposed rat kidney resemble more closely those predicted by the partial obstruction rather than by the increased compliance hypothesis of renal cyst formation. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Electric Literature of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Electric Literature of C15H12N2S

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