Tag: 100-200

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

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

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

Thiazolocyanines. XII. Polar substituents in thiazole rings of thiazolocyanines was written by Sych, E. D.;Umanskaya, L. P.. And the article was included in Zhurnal Obshchei Khimii in 1964.Electric Literature of C4H6N2S This article mentions the following:

Spectra of thiazolocyanines showed that the conjugation of electroneg. groups in the 5-position of the thiazole ring in thiazolocyanines with the rest of the mol. is developed more effectively than that of the electropos. groups in the 5-position or of electroneg. groups in the 4-position. Bromination of 2-methylthiazole in AcOH gave 2-methyl-5-bromothiazole (I); MeI adduct m. 243°; the Me tosylate (undescribed) was prepared from p-MeC₆H₄SO₃Me at 90°. Refluxing 2-mercapto-5-acetamidothiazole with MeI in EtOH for 10 min. gave 2-(methylthio)-5-acetamidothiazole (II) m. 144°; the methiodide was prepared conventionally. NCCH₂NH₂.H₂SO₄ treated with aqueous KOH, followed by MeCS₂K for 10 hrs., gave a low yield of 2-methyl-5-aminothiazole, m. 110°; Ac₂O gave the 5-acetamido analog, m. 144°; the Et tosylate was prepared conventionally. I heated for 10 min. at 160° with PhN:CHOEt (III) followed by 0.5 hr. at 140° gave 2-(2-anilinovinyl)-5-bromothiazole Me tosylate, which with I Et tosylate in Ac₂O-Et₃N-EtOH for 5 min. gave after addition of NaClO₄ bis[3-methyl-5-bromo-2-thiazole]trimethinecyanine perchlorate, m. 183-4°, λ_maximum 566 mμ. 2,4-Dimethyl-5-acetylthiazole-EtI and EtOCH:C(CO₂Et)₂ in EtOH-Et₃N for 0.5 hr. gave bis[3-ethyl-4-methyl-5-acetyl-2-thiazole]trimethinecyanine iodide, m. 240°, λ_maximum 598 mμ. I Me tosylate and 2-(methylthio)benzothiazole Et tosylate similarly gave after addition of KI, yellow [3-methyl-5-bromo-2-thiazole] – [3 – ethyl – 2 – benzothiazole]methinecyanine iodide, m. >320°, λ_maximum 423 mμ. II Et tosylate and 2-methylbenzothiazole Et tosylate similarly gave yellow [3-ethyl-5-acetamido-2-thiazole] – [3-ethyl- 2- benzothiazole]methinecyanine tosylate, m. 235°, λ_maximum 434 mμ. Similarly, quinaldine Et tosylate gave red [3-methyl-5-acetamido-2-thiazole] – [3-ethyl-2-quinoline]methinecyanine iodide, m. 282°, λ_maximum 489 mμ. 2-Methyl-5-aminothiazole-MeI and 2-(methylthio)benzothiazole Et tosylate rapidly gave orange [3-methyl-5-amino-2-thiazole]-[3-ethyl-2-benzothiazole]methinecyanine iodide, m. 245°, λ_maximum 457 mμ. 2-Methyl-thiazole Me tosylate and III at 160° gave 81% 2-(2-anilinovinyl)-thiazole Me tosylate, which was directly treated with 3-ethyl-rhodanine in Ac₂O-Et₃N-EtOH and gave in 1 hr. 3-ethyl-5-[(3-methyl-2-thiazolinylidene)ethylidene]thiazolidine-2-thion-4-one, m. 220-1°, λ_maximum 535 mμ. 2-(2-Anilinovinyl)-5-bromothiazole Me tosylate similarly gave blue 3-ethyl-5-[(3-methyl-5-bromo-2-thiazolinylidene)ethylidene] thiazolidine-2-thion-4-one, m. 168°, λ_maximum 537 mμ. 2-Methyl-5-carbethoxythiazole and HC(OEt)₃ refluxed in pyridine 40 min. and treated with KI gave violet bis-[3-ethyl-5-carbethoxy-2-thiazole]trimethinecyanine iodide, m. 134°, λ_maximum 583 mμ. Similarly, 2-methyl-4-carbethoxythiazole Et tosylate gave bis[3-ethyl-4-carbethoxy-2-thiazole]trimethinecyanine iodide, m. 173° λ_maximum 542 mμ. 2-Ethyl-5-carbethoxythiazole Et tosylate and 2-(methylthio)benzothiazole Et tosylate in EtOH-Et₃N gave after addition of KI yellow [3-ethyl-5-carbethoxy-2-thiazole]-[3-ethyl-2-benzothiazole]methinecyanine iodide, m. 202°, λ_maximum 428 mμ. Similarly, 2-methyl-5-carbomethoxythiazole Et tosylate gave [3-ethyl-5-carbomethoxy-2-thiazole]-[3-ethyl-2-benzothiazole]methinecyanine tosylate, m. 233°, λ_maximum 430 mμ. II Et tosylate and 3-ethylrhodanine refluxed 10 min. in pyridine gave orange 3-ethyl-5-[3-ethyl-5-acetamido-2-thiazo-linylidene]thiazolidine-2-thion-4-one, m. 234-5°, λ_maximum 443 mμ. I Et tosylate and p-Me₂NC₆H₄CHO refluxed in Ac₂O gave with KI gave violet 2-(p-dimethylaminostyryl)-5-bromothiazole-MeI, m. 238°, λ_maximum 510 mμ; similarly prepared was 78% violet 2-(p-dimethylaminostyryl)-6-bromobenzothiazole Et tosylate, m. 272°, λ_maximum 540 mμ. 2-Methyl-5-acetamidothiazole Et tosylate and HC(OEt)₃ heated in PhNO₂ and treated with NaClO₄ gave bis[3-ethyl-5-acetamido-2-thiazole]trimethinecyanine perchlorate, λ_maximum 576 mμ. Similarly was prepared rather unstable bis[3-methyl-5-amino-2-thiazole]trimethinecyanine tosylate, λ_maximum 580 and 530 mμ, which lost the longer wavelength maximum on standing. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Electric Literature of C4H6N2S).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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. 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.Electric Literature of C4H6N2S

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

Discovery of Piperazin-1-ylpyridazine-Based Potent and Selective Stearoyl-CoA Desaturase-1 Inhibitors for the Treatment of Obesity and Metabolic Syndrome was written by Zhang, Zaihui;Sun, Shaoyi;Kodumuru, Vishnumurthy;Hou, Duanjie;Liu, Shifeng;Chakka, Nagasree;Sviridov, Serguei;Chowdhury, Sultan;McLaren, David G.;Ratkay, Leslie G.;Khakh, Kuldip;Cheng, Xing;Gschwend, Heinz W.;Kamboj, Rajender;Fu, Jianmin;Winther, Michael D.. And the article was included in Journal of Medicinal Chemistry in 2013.Name: Thiazol-2-ylmethanamine This article mentions the following:

Stearoyl-CoA desaturase-1 (SCD1) catalyzes de novo synthesis of monounsaturated fatty acids from saturated fatty acids. Studies have demonstrated that rodents lacking a functional SCD1 gene have an improved metabolic profile, including reduced weight gain, lower triglycerides, and improved insulin response. In this study, we discovered a series of piperazinylpyridazine-based highly potent, selective, and orally bioavailable compounds Particularly, compound I (XEN103) was highly active in vitro (mSCD1 IC₅₀ = 14 nM and HepG2 IC₅₀ = 12 nM) and efficacious in vivo (ED₅₀ = 0.8 mg/kg). It also demonstrated striking reduction of weight gain in a rodent model. Our findings with small-mol. SCD1 inhibitors confirm the importance of this target in metabolic regulation, describe novel models for assessing SCD1 inhibitors for efficacy and tolerability and demonstrate an opportunity to develop a novel therapy for metabolic disease. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Name: Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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.Name: Thiazol-2-ylmethanamine

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

Influence of steric factors on the interaction of isomeric phenyloxazoles and phenylthiazoles with microsomal oxidation was written by Smith, Leverett R.;Wilkinson, Christopher F.. And the article was included in Biochemical Pharmacology in 1978.Recommanded Product: 5-Phenylthiazole This article mentions the following:

5-Phenyloxazole (I) [1006-68-4] and 5-phenylthiazole (II) [1826-13-7] showed a high inhibitory activity and low spectral (type II) dissociation (K_s) towards both rat liver microsomal and armyworm midgut preparations 4-Phenyloxazole [20662-89-9] had a high K_s, and 2-phenyloxazole [20662-88-8], 4-phenylthiazole [1826-12-6], 2-phenylthiazole (III) [1826-11-5], benzoxazole [273-53-0], and benzothiazole [95-16-9] showed little spectral interactions with microsomes; none other than III had any significant inhibitory effects. The lack of type II binding by III suggests that its mode of action differs from that of I and II. The results are consistent with the steric model developed previously with the imidazoles. 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 are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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

Thermal analyses and spectral characterization of some synthesized metal(II) Schiff base complexes was written by Jain, Rajendra K.;Mishra, A. P.;Gupta, Priya. And the article was included in Journal of Thermal Analysis and Calorimetry in 2012.Category: thiazole This article mentions the following:

Schiff base metal complexes derived from 2-thiophenecarboxylidine-4-anisidine, 3,4-dihydroxy-5-nitrobenzylidine-2-amino-5-methylthiazole and 3,4-dihydroxy-5-nitrobenzylidine-4-chloroaniline were synthesized and characterized by elemental anal., IR, UV-visible, molar conductance and thermal analyses. The complexes are colored and stable in air at room temperature The complexes exhibit coordination number to be 4 and 6. The thermal behavior of metal complexes shows that the hydrated complexes lose water mols. of hydration in the first and then is immediately followed by decomposition of ligand mols. in the subsequent steps. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Category: thiazole).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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.Category: thiazole

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

Transmission of substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance. Benzothiazoles was written by Sawhney, Shanti N.;Boykin, David Withers. And the article was included in Journal of Organic Chemistry in 1979.Application of 68867-17-4 This article mentions the following:

The carbon-13 NMR spectra of 57 benzothiazoles, including 6-substituted 2-aminobenzothiazoles (I), 6-substituted 2-methylbenzothiazoles (II), 6-substituted benzothiazoles (III), 5-substituted 2-methylbenzothiazoles (IV), and 2-substituted benzothiazoles (V) were determined in (CD₃)₂SO. Single and dual parameter correlations of the chem. shifts with substituent constants were described for C-2 and C-9 of I, II, and III and for C-2 and C-3 of IV. Resonance effects are primarily responsible for the substituent effect on chem. shifts at these carbons. Transmission of substituent effects by the atom is limited, and the primary path of transmission to C-2 is through N. The data from series III and V suggest that transmission of substituent effects from C-2 to C-6 is ∼1/3 less effective than transmission from C-6 to C-2. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Application of 68867-17-4).

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). 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.Application of 68867-17-4

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

Design and Synthesis of New Pyrazole-Based Heterotricycles and their Derivatization by Automated Library Synthesis was written by Fricero, Prisca;Bialy, Laurent;Czechtizky, Werngard;Mendez, Maria;Harrity, Joseph P. A.. And the article was included in ChemMedChem in 2020.COA of Formula: C4H6N2S This article mentions the following:

This work highlighted how a readily assembled N-hydroxyethyl pyrazole trifluoroborate offered rapid access to architecturally distinct 5-6-6- and 5-7-6-fused tricyclic compounds such as I [R = F, NO₂, CO₂H, etc.] and II [R¹ = NEt₂, N-morpholino, NHCH₂-2-pyridyl, etc.]. This chem. was not only amenable to single compound synthesis, but also to high-throughput experimentation. It give easy access to diverse compound arrays with various physicochem. and ADME profiles by fully automated library synthesis. The combination of the high-throughput experimentation with rapid testing of the compounds in an integrated physicochem. and ADME profiling workflow allowed accelerated design of novel lead compounds in drug-discovery projects. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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 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.COA of Formula: C4H6N2S

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

Copper(II)-Mediated Dehydrogenative Cross-Coupling of Heteroarenes was written by Mao, Zhifeng;Wang, Zhe;Xu, Zhaoqing;Huang, Fei;Yu, Zhengkun;Wang, Rui. And the article was included in Organic Letters in 2012.Related Products of 1826-13-7 This article mentions the following:

Cu(OAc)₂-mediated dehydrogenative cross-coupling between two heteroarenes has been realized in the absence of any other additive. A mechanism involving a formal Cu(II) to Cu(0) route by convergent disproportionation of the copper mediator is proposed and has been evidenced by copper mirror formation during the reaction. This synthetic protocol provides a concise and “green” access to unsym. biheteroarenes bearing structural motifs of substantial utility in organic synthesis. 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. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.Related Products of 1826-13-7

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