Category: thiazole

Nucleophilic addition of 2-phenylaminobenzothiazole to acrylic acid was written by Saprykina, V. A.;Ambartsumova, R. F.. And the article was included in Uzbekskii Khimicheskii Zhurnal in 1987.Category: thiazole This article mentions the following:

Addition of CH₂:CHCO₂H to 2-anilinobenzothiazole 5 h at 140° gave 57% benzothiazole I and 14% benzothiazoline II. Amination of 2-chlorobenzothiazole with PhNHCH₂CH₂CO₂Me gave the Me ester of I which was saponified by H₂SO₄. 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. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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

Site-selective acylation of carbohydrates directed by recyclable polymer-supported isothiourea catalysts was written by Song, Wang-Ze;Dong, Kun;Li, Ming;Li, Jun-Hao;Ullah, Karim;Zheng, Yu-Bin. And the article was included in Heterocycles in 2019.COA of Formula: C7H3BrClNS This article mentions the following:

The polystyrene-supported isothiourea catalysts, derived from the homogeneous catalyst BTMs, were synthesized and applied to the site-selective acylation of carbohydrates. The catalysts can be recovered and reused conveniently for 10 cycles without significantly loss in either activity or selectivity. It offers a sustainable and environmentally benign approach for the site-selective functionalization of carbohydrates. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4COA of Formula: C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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 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.COA of Formula: C7H3BrClNS

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

The 1:2 molar adducts in the reaction of 5-phenylthiazole and dimethyl acetylenedicarboxylate was written by Maeda, Minoru;Ito, Shigeru;Kojima, Masaharu. And the article was included in Tetrahedron Letters in 1976.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

5-Phenylthiazole with MeO2CCCCO2Me in a 1:2 molar ratio at 60° for 2 hr gave three isomeric products: I (R = CO2Me, R1 = H; R = H, R1 = CO2Me) (II and III, resp.) and IV. III on heating in C6H6 at 130° for 12 hr gave 7.7% II and 32% IV, whereas II gradually isomerized at room temperature or in C6H6 at 130° to give IV. The results indicate that II and III are the initial addition products arising from the same zwitterion intermediate and that IV is produced directly from II. The isomerization of III to II and IV would proceed through the common intermediate and not by successive [1,5]-sigmatropic shifts. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).

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. 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.Application In Synthesis of 5-Phenylthiazole

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

Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines was written by Xu, Yuanshuang;Li, Bin;Zhang, Xinying;Fan, Xuesen. And the article was included in Journal of Organic Chemistry in 2017.Formula: C13H10N2S This article mentions the following:

In this paper, a highly efficient and sustainable synthesis of 2-aminobenzothiazoles through the cascade reactions of isothiocyanatobenzenes with primary or secondary amines by using iodine as a catalyst and oxygen as an oxidant is presented. Mechanistically, the formation of the title compounds involves the in situ formation of the required benzothiourea intermediate followed by its intramol. cross dehydrogenative coupling of a C(sp²)-H bond and a S-H bond. To our knowledge, this should be the first example in which 2-aminobenzothiazoles are efficiently prepared from simple and cheap isothiocyanates and amines under metal-free conditions by using iodine as a catalyst and mol. oxygen as an oxidant with water as the byproduct. Compared with literature protocols, this method eliminates the use of ortho-halo-substituted precursors, expensive transition-metal catalysts, and hazardous oxidants. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: C13H10N2S).

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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C13H10N2S

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

Molecular search of new active drugs against Toxoplasma gondii was written by Gozalbes, R.;Galvez, J.;Garcia-Domenech, R.;Derouin, F.. And the article was included in SAR and QSAR in Environmental Research in 1999.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Mol. connectivity has been applied to the search of new compounds with activity against the protozoan Toxoplasma gondii, using a stepwise linear discriminant anal. (SLDA) which is able to classify a compound according to its activity either as active or as inactive. Among the selected compounds, andrographolide and dibenzothiophene sulfone stand out, both with IC₅₀ values lower than 1 μg/mL, which are comparable to these of drugs such as sulfamethoxazole, pyrimethamine and trimethoprim, with IC₅₀ values equal to 1.1, 0.04 and 2.31 μg/mL, resp. These results confirm the usefulness of this topol. approach for the selection and design of new-lead drugs active against Toxoplasma gondii. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

A one-pot strategy for the synthesis of 2-aminobenzothiazole in water by copper catalysis was written by Khatun, Nilufa;Jamir, Latonglila;Ganesh, Majji;Patel, Bhisma K.. And the article was included in RSC Advances in 2012.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A straightforward, efficient and sustainable method (green chem.) for the synthesis of 2-aminobenzothiazole derivatives has been achieved from in-situ generated 2-halo thioureas using a copper(I) catalyst in water as a reaction medium. The present study demonstrates that copper iodide (CuI) exhibits better efficiency in water towards intramol. S-arylation compared to other organic solvents. While (2-iodoaryl)thioureas are smoothly converted to the desired product in high yield with only a catalytic quantity of CuI, addition of base and ligand are essential for bromo analogs and chloro analogs. The title compounds thus formed included N-(2-methoxyphenyl)-2-benzothiazolamine (I) [N-(2-methoxyphenyl)-6-methyl-2-benzotiazolamine]. An unprecedented demethoxylation of a (2-methoxyphenyl)thiourea intermediate followed by a Friedel-Crafts type methylation (para to nitrogen) was observed in the aryl ring possessing the original methoxy group and the product thus formed was N-(2-iodo-4-methylphenyl)-6-methyl-2-benzotiazolamine (II). The synthesis of the target compounds was also achieved by a reaction of 1-iodo-2-(isothiocyanato)benzene with morpholine, piperidine, pyrrolidine and the products thus formed included 2-(4-morpholinyl)benzothiazole, 2-(1-piperidinyl)benzothiazole and 2-(1-pyrrolidinyl)benzothiazole. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).

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

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

Experimental model of renal tumors in polycystic kidneys: effects of long-term 2-amino-4,5-diphenylthiazole administration in rats treated with N-ethyl-N-hydroxyethylnitrosamine was written by Tsumatani, Kenichi;Nakagawa, Yoshinori;Kitahori, Yoshiteru;Konishi, Noboru;Uemura, Hirotsugu;Ozono, Seiichiro;Hirao, Yoshihiko;Okajima, Eigoro;Hirao, Kazuya;Hiasa, Yoshio. And the article was included in Toxicologic Pathology in 1997.Category: thiazole This article mentions the following:

The present study was undertaken to examine the effects of long-term 2-amino-4,5-diphenylthiazole (DPT) treatment after initiation of kidney carcinogenesis with N-ethyl-N-hydroxyethylnitrosamine (EHEN) in Wistar rats. One hundred forty-four 6-wk-old male Wistar rats were divided into 6 equal receiving groups: 1000 ppm EHEN or normal tap water for 2 wk followed by 1.06% DPT or basal diet for the subsequent 14 or 30 wk. Controls were maintained without treatment throughout. Subgroups of 6 animals from each group were sacrificed after 8, 16, 24, and 32 wk for histopathol. assessment of lesion development in the kidneys and liver. Animals treated with DPT first developed cystic changes of the kidneys (primarily at the corticomedullary border) after 8 wk of treatment, and these changes progressed with time thereafter. In the groups in which DPT treatment was discontinued after 14 wk, cysts then gradually decreased in size. All tumors detected in the kidneys were histopathol. diagnosed as renal cell adenomas. The tumor multiplicity after 32 wk of treatment was significantly higher in Group I, receiving EHEN + DPT for 30 wk (6.33±4.46), and Group III, receiving EHEN + DPT for 14 wk (3.83±1.57), than in Group V, EHEN alone (1.00±0.58). Renal cell tumors within cysts were only seen in Groups I and III. The general bromodeoxyuridine labeling indexes for the kidneys at week 32 were significantly higher in Group I (55.94±21.08 cells/mm²) and Group III (53.75±12.38 cells/mm²) than in Group V (22.38±6.98 cells/mm²). In conclusion, DPT caused cystic changes in rat kidneys, which, however, gradually decreased in size after the treatment was discontinued, suggesting a reversible nature. DPT clearly also promotes renal tumor development after EHEN initiation, and this effect persists, to a certain extent, even after the insult is removed. 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. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Category: thiazole

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

Importance of substituents in ring opening: a DFT study on a model reaction of thiazole to thioamide was written by Bai, Xue;Qin, Dan;Yang, Lijun. And the article was included in Journal of Molecular Modeling in 2021.Recommanded Product: 2-Methylthiazol-5-amine This article mentions the following:

Thiazole ring is an important active mol. skeleton of drugs. Thiazole in natural products and drugs are usually harmlessly eliminated. However, hepatotoxic reactions may occur due to the biol. activation of thiazole to produce reactive thioamide. A typical example is hepatotoxic sudoxicam and safety meloxicam. The only structural difference between them is a Me group on C5 position of thiazole in meloxicam. The mol. basis for the difference remains unknown and the bioactivation mechanism of the thiazole ring is still obscure. Quantum chem. calculations were performed to elucidate the activation mechanism of the thiazole ring under P 450 catalysis, and the influence of the substituents on the activation pathways of thiazole ring was also studied. The calculated results show that the activation of thiazole is closely related to the substituents on the thiazole and spin state of Cpd I. The thiazole and substituted thiazole directly open the ring when catalyzed by doublet spin state Cpd I that catalyzed by the quartet spin state Cpd I can open the ring directly or indirectly, which is related to the substituents. Thiazoles modified with electron-donating substituents mainly undergo direct ring opening, while thiazoles modified with electron-withdrawing groups or weak electron-donating groups mainly undergo indirect ring-opening process accompanied by intermediate formation. The research results laid the foundation for the design of thiazole ring drugs, and also laid a theor. foundation for the study of reducing the toxicity of thiazole ring drugs. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Recommanded Product: 2-Methylthiazol-5-amine).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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.Recommanded Product: 2-Methylthiazol-5-amine

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

Regarding the synthesis of 2-mercaptobenzothiazole was written by Ivanova, V. A.;Shebuev, A. N.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1957.Application of 1843-21-6 This article mentions the following:

A series of preparations were made in an attempt to establish the progressive steps in the synthesis of 2-mercaptobenzothiazole (I) from PhNH₂, CS₂, and S at 250°. The reactions of PhNH₂ and CS₂ to form (PhNH)₂CS (II) or PhNCS (III) and H₂S are reversible. The former decompose above 160° to form the original substances and the latter, though stable, reacts with S to form I only in the presence of saponifying agents. Neither II nor III can, therefore, be intermediate steps in the synthesis of I (cf. Sebrell and Boord, C.A. 17, 3876; Bruni and Levi, C.A. 18, 2341). Their presence in the products at certain stages of the reaction is attributed to side reactions. Heating 2-aminothiophenol (IV) or 2,2′-diaminodiphenyl disulfide (V) with S failed to yield acylated compounds This was probably due to the rapid closing of the thiazole ring to give I. On the other hand, in an alk. solution, IV reacts with CS₂ at 80° to give C₁₃H₁₀N₂S₃ which reacts with Zn dust and HCl to give 4,4′-dimercaptodiphenylthiourea. By analogy it was assumed that CS₂ acylates the amino group of IV or V which pass into I. PhNH₂, CS₂, and S were heated in an autoclave 3 hrs. at 250-60° and then cooled to 20°. After treatment with dilute HCl and recrystallization from 50% EtOH, V was obtained, m. 93°. The absence of IV and the presence of a considerable quantity of anilinobenzothiazole (VI) in the products were noted. The absence of IV was ascribed to its oxidation by S; at 20° S dissolved in IV with a vigorous evolution of H₂S and the formation of V. The presence of VI was ascribed to the reversible reaction PhNH₂ + I ⇌ VI + H₂S which is shifted to the left as the normal synthesis progresses and PhNH₂ is used up. VI is not an intermediate in the synthesis of I. 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 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.Application of 1843-21-6

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

Parallel solution-phase synthesis of a 2-aminothiazole library including fully automated work-up was written by Buchstaller, Hans-Peter;Anlauf, Uwe. And the article was included in Combinatorial Chemistry & High Throughput Screening in 2011.Electric Literature of C15H12N2S This article mentions the following:

A straightforward and effective procedure for a solution phase preparation of a 2-aminothiazole combinatorial library is described. The synthesis of the target compounds was achieved by a reaction, work-up and isolation of these thiazolamine derivatives as free bases by a fully automated method using the Chemspeed ASW 2000 automated synthesizer. The compounds were obtained in good yields and excellent purity without any further purification requirements. 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 thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Electric Literature of C15H12N2S

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