Category: thiazole

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I₂/dimethyl sulfoxide as a catalytic oxidative system was written by Zhang, Qian;Wu, Jiefei;Pan, Zexi;Zhang, Wen;Zhou, Wei. And the article was included in Journal of Chemical Research in 2021.SDS of cas: 6318-74-7 This article mentions the following:

A series of 2-aminothiazoles was prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I₂/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus provided a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7SDS of cas: 6318-74-7).

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

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

Selective Detection of 5-Formyl-2′-deoxyuridine, an Oxidative Lesion of Thymidine, in DNA by a Fluorogenic Reagent was written by Hirose, Wataru;Sato, Kousuke;Matsuda, Akira. And the article was included in Angewandte Chemie, International Edition in 2010.Formula: C9H10N2O2S This article mentions the following:

The authors report a new concept for the simple detection of 5-Formyl-2′-deoxyuridine (fodUrd) in damaged DNA with a fluorogenic reagent. The reagent 2-amino-4,5-dimethoxythiophenol (I) shows no fluorescence before reaction with the target fodUrd in DNA. However, upon the reaction of I with fodUrd, the formyl group at the 5-position of fodUrd is converted into a benzothiazol-2-yl group, which is directly conjugated with the uracil group. This ring system is similar to luciferin, which undergoes the luciferase reaction to produce luminescence. Thus, fodUrd in DNA could be detected directly by fluorescence measurement without enzymic hydrolysis of the target DNA to its corresponding nucleosides, HPLC separation, and anal. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Formula: C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C9H10N2O2S

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

Photochemistry of 3- and 5-Phenylisothiazoles. Competing Phototransposition Pathways was written by Pavlik, James W.;Tongcharoensirikul, Pakamas. And the article was included in Journal of Organic Chemistry in 2000.Synthetic Route of C9H7NS This article mentions the following:

5-Phenylisothiazole undergoes phototransposition via the electrocyclic ring closure-heteroatom migration pathway and by the N₂-C₃ interchange reaction pathway. The latter route is enhanced by the addition of triethylamine (TEA) to the reaction medium and by increasing the polarity of the solvent. In addition to phototransposition, 5-phenylisothiazole also undergoes photocleavage to 2-cyano-1-phenylethenethiol which was trapped by reaction with benzyl bromide to yield 2-cyano-1-phenylethen-1-yl benzyl thioether. 3-Phenylisothiazole also phototransposes by both reaction pathways, but the product distribution is not affected by the addition of TEA or by changing the solvent polarity. 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 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.Synthetic Route of C9H7NS

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

Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement was written by Zambon, Alfonso;Borsato, Giuseppe;Brussolo, Stefania;Frascella, Pietrogiulio;Lucchini, Vittorio. And the article was included in Tetrahedron Letters in 2008.COA of Formula: C9H7NS This article mentions the following:

A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metalated thiazoles by tuning the reaction conditions. The proposed mechanism, based on exptl. evidence, is characterized by the catalytic role of thiazole bisadducts as metal-transfer agents. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: 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.COA of Formula: C9H7NS

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

Thiazole Orange derivatives: Synthesis, fluorescence properties, and labeling cancer cells was written by Fei, Xuening;Gu, Yingchun;Ban, Ying;Liu, Zhijun;Zhang, Baolian. And the article was included in Bioorganic & Medicinal Chemistry in 2009.Recommanded Product: 5-Nitrobenzothiazole-2-thiol This article mentions the following:

A series of Thiazole Orange (TO) derivatives were synthesized and modified by introducing different substitutional groups on benzothiazole and 4-methylquinoline. All the TO derivatives were confirmed by ¹H NMR and MS. TO derivative bearing NH₂– was modified by folic acid and used to label breast cancer cells. The phenomenon of fluorescence enhancement was shown by the fluorescence spectra of TO derivatives and micrographs of the labeled breast cancer cells. It offered a new try in the aspect of labeling cells by the embedded dyes. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Recommanded Product: 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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.Recommanded Product: 5-Nitrobenzothiazole-2-thiol

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

Identification of G protein-coupled receptor 120-selective agonists derived from PPARγ agonists was written by Suzuki, Takayoshi;Igari, Sou-ichi;Hirasawa, Akira;Hata, Mie;Ishiguro, Masaji;Fujieda, Hiroki;Itoh, Yukihiro;Hirano, Tatsuya;Nakagawa, Hidehiko;Ogura, Michitaka;Makishima, Makoto;Tsujimoto, Gozoh;Miyata, Naoki. And the article was included in Journal of Medicinal Chemistry in 2008.Application of 1843-21-6 This article mentions the following:

A weak, nonselective G protein-coupled receptor 120 (GPR120) agonist 10 was found by screening a series of carboxylic acids derived from the peroxisome proliferator-activated receptor γ (PPARγ) agonist 3. Modification based on the homol. model of GPR120 led to the first GPR120-selective agonist 12. These results provide a basis for constructing new tools for probing the biol. of GPR120 and for developing new candidate therapeutic agents. 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. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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 of 1843-21-6

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

Dehydration Polymerization for Poly(hetero)arene Conjugated Polymers was written by Mirabal, Rafael A.;Vanderzwet, Luke;Abuadas, Sara;Emmett, Michael R.;Schipper, Derek. And the article was included in Chemistry – A European Journal in 2018.SDS of cas: 1826-13-7 This article mentions the following:

The lack of scalable and sustainable methods to prepare conjugated polymers belies their importance in many enabling technologies. Accessing high-performance poly(hetero)arene conjugated polymers by dehydration has remained an unsolved problem in synthetic chem. and has historically required transitional-metal coupling reactions. Herein, we report a dehydration method that allows access to conjugated heterocyclic materials. By using the technique, we have prepared a series of small mols. and polymers. The reaction avoids using transition metals, proceeds at room temperature, the only required reactant is a simple base and water is the sole byproduct. The dehydration reaction is tech. simple and provides a sustainable and straightforward method to prepare conjugated heteroarene motifs. 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. 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.SDS of cas: 1826-13-7

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

Synthesis and evaluation of some benzothiazole derivatives as antidiabetic agents was written by Kumar, Sunil;Rathore, D. S.;Garg, Gopal;Khatri, Kapil;Saxena, Rahul;Sahu, Sanjeev K.. And the article was included in International Journal of Pharmacy and Pharmaceutical Sciences in 2017.Synthetic Route of C7H4N2O2S2 This article mentions the following:

A novel series of benzothiazole derivatives I (R¹ = H, CH₃, NO₂; R² = H, NO₂; R³ = C₆H₅, p-HOC₆H₄, p-CH₃OC₆H₄, m-O₂NC₆H₄) were synthesized and subsequently assayed in vivo to investigate their hypoglycemic activity by the alloxan-induced diabetic model in rats. All the synthesized derivatives showed significant biol. efficacy. Among the synthesized compounds, I (R¹ = CH₃; R² = H; R³ = m-O₂NC₆H₄) at 350 mg/kg exerted maximum glucose lowering effects whereas compound I (R¹ = CH₃; R² = H; R³ = p-CH₃OC₆H₄) showed min. glucose lowering effects. All compounds were effective, and exptl. results were statistically significant at p<0.01 and p<0.05 level. From the results, it is clear that compound I (R¹ = CH₃; R² = H; R³ = m-O₂NC₆H₄) demonstrated potent anti-diabetic activity and would be of better use in drug development to combat the metabolic disorder in future. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Synthetic Route of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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. 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 C7H4N2O2S2

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

Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition-cyclization was written by Huynh, Thao Nguyen Thanh;Tankam, Theeranon;Koguchi, Shinichi;Rerkrachaneekorn, Tanawat;Sukwattanasinitt, Mongkol;Wacharasindhu, Sumrit. And the article was included in Green Chemistry in 2021.Synthetic Route of C13H10N2S This article mentions the following:

An electrochem. synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl cooperatively in catalytic amounts, electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).

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. 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 C13H10N2S

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

Studies on chalcogen-containing heterocycles. 35. Rapid one-pot versatile preparation of 2-aminobenzothiazoles by highly efficient copper(I)-catalyzed inorganic base-free intramolecular cyclization was written by Sashida, Haruki;Kaname, Mamoru. And the article was included in Heterocycles in 2012.Computed Properties of C13H10N2S This article mentions the following:

A convenient and versatile 1-pot preparation of 2-aminobenzothiazoles by the efficient Cu(I)-catalyzed intramol. cyclization of com. available 2-RC₆H₄NCS (R = I, Br, Cl) with N-nucleophiles was accomplished. The reaction proceeded under inorganic-base-free conditions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

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. 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 C13H10N2S

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