Heterocyclic Building Blocks-Thiazole

Study on electron-impact fragmentation of benzothiazole derivatives was written by Claude, Saturnin;Tabacchi, Raffaele;Duc, Laurent;Fuchs, Rudolf;Boosen, Karl-Josef. And the article was included in Helvetica Chimica Acta in 1980.Related Products of 1843-21-6 This article mentions the following:

The mass spectra of 18 title compounds, all thermodn. stable, show intense mol. ions whose fragmentations are substituent dependent; the substituent is rarely lost in the initial fragmentations. β-Cleavage, with respect to the heterocyclic double bond, is often observed 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. 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.Related Products of 1843-21-6

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

Room-Temperature Ligand-Free Pd/C-Catalyzed C-S Bond Formation: Synthesis of 2-Substituted Benzothiazoles was written by Cheng, Yannan;Peng, Qian;Fan, Weigang;Li, Pixu. And the article was included in Journal of Organic Chemistry in 2014.Electric Literature of C13H10N2S This article mentions the following:

The synthesis of 2-substituted benzothiazoles has been achieved via cyclization of o-iodothiobenzanilide derivatives using Pd/C as the catalyst at room temperature The protocol is ligand-free, additive-free, and high-yielding and involves very mild conditions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Electric Literature 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. 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.Electric Literature of C13H10N2S

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

Synthesis of 5-arylthiazole derivatives by a ring closure of thioformamido ketones was written by Ohta, Masaki. And the article was included in Yakugaku Zasshi in 1951.Recommanded Product: 1826-13-7 This article mentions the following:

KOH (23 g.) in 80 mL. MeOH is divided into 2 portions, one of which is saturated with H₂S and the other poured into it, heated to 50°, the mixture treated with 15 g. CHCl₃ through the reflux condenser, let stand l0 min., filtered, and the MeOH removed in vacuo, yielding 30% HCS₂K (I). Treating 5 g. BzCH₂NH₂.HCl in 50 mL. water with aqueous I (prepared from 23 g. KOH) 1 h. at room temperature, filtering, and washing with water gives 4.7 g. (95%) HCSNHCH₂Bz (II), needles, m. 108°. II (1.2 g.) in 3 mL. concentrated H₂SO₄ into water after 30 min., neutralized with NH₄OH, and steam-distilled gives 1 g. 5-phenylthiazole (III), m. 45-6°; picrate, decompose 136-7°. III (10 g.) in 40 mL. concentrated H₂SO₄ treated with 24 mL. concentrated H₂SO₄ and 16 mL. fuming HNO₂ with cooling to 0°, poured in water, filtered, and washed with water gives 12 g. 5-(p-nitrophenyl)thiazole (IV), m. 145-6°. Reduction of 5 g. IV in a 15 mL. water, containing 2 g. NH₄Cl and 20 g. Fe 2 h. at 80° gives 2 g. 5-(p-aminophenyl)thiazole (V), m. 149°. Decylamine-HCl (2 g.) and aqueous I (from 8 g. KOH) give 1.8 g. N-thioformyldecylamine (VI), m. 172°. VI (0.5 g.) in 8 g. concentrated H₂SO₄ poured into water gives 0.3 g. 4, 5-diphenylthiazole, m. 63-4°. m-O₂NC₆H₄COCH₂NH₂.HCl (0.7 g.) in 20 mL. water and aqueous I (from 2.3 g. KOH) give 0.5 g. m-nitro-α-thioformamidoacetophenone (VII), decompose 159-60°. Treating VII with concentrated H₂SO₄ as in the preparation of III gives 5-(m-nitrophenyl)thiazole, m. 59°. p-ClC₆H₄COCH₂NH₂.HCl (3 g.) and aqueous I (from 12 g. KOH) give 1.5 g. HCSNHCH₂COC₆H₄Cl (VIII), decompose 147°; treating VIII with concentrated H₂SO₄ as in the preparation of III gives 5-(p-chlorophenyl)thiazole, m. 40°; picrate, decompose 168°. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 1826-13-7).

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 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.Recommanded Product: 1826-13-7

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

One-pot synthesis of 2-aminothiazoles using supported reagents was written by Kodomari, Mitsuo;Aoyama, Tadashi;Suzuki, Yoshitada. And the article was included in Tetrahedron Letters in 2002.Recommanded Product: 6318-74-7 This article mentions the following:

A simple and efficient method was developed for the synthesis of 2-aminothiazoles from α-bromo ketones in 1-pot using a supported reagents system, KSCN/SiO₂-RNH₃OAc/Al₂O₃, in which α-bromo ketone reacts 1st with KSCN/SiO₂ and the product, α-thiocyano ketone, reacts with RNH₃OAc/Al₂O₃ to give the final product, 2-aminothiazole, in high yield. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 6318-74-7

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

Reinvestigation of reactions of thiazolium and benzothiazolium N-phenacylides with electron-deficient acetylenes was written by Iwamura, Tatsunori;Kobayashi, Masahiro;Ichikawa, Takashi;Shimizu, Hiroshi;Kataoka, Tadashi. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry in 1996.Computed Properties of C9H7NS This article mentions the following:

Reactions of thiazolium and benzothiazolium N-phenacylides with di-Me acetylenedicarboxylate (DMAD) have been reexamined The thiazolium N-phenacylides generated in situ from 4-methyl- or 5-phenyl-3-phenacylthiazolium bromides with triethylamine, reacted with DMAD in dry DMF to give the thiazole ring-opened products I (R = Me, H; R¹ = H, Ph; R² = H, Br, NO₂) in which two mols. of DMAD had been incorporated. The reactions when conducted in both aqueous DMF and in dry DMF in the presence of lithium perchlorate gave the hemithioacetals II which could be transformed into the 1:2 reaction products I of the ylides and DMAD. Benzothiazolium N-phenacylides similarly reacted with DMAD to afford the 1:2 reaction products I (RR¹ = CH=CHCH=CH; R² = H, Br) or the hemithioacetals II. 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. 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.Computed Properties of C9H7NS

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

A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41 was written by Xiao, Ruian;Hao, Wenyan;Ai, Jinting;Cai, Ming-Zhong. And the article was included in Journal of Organometallic Chemistry in 2012.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The heterogeneous tandem reactions of 2-haloanilines with isothiocyanates were achieved in DMSO using Et₃N as base at 80 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(II) complex [MCM-41-2N-CuSO₄], yielding a variety of 2-aminobenzothiazoles in good to excellent yields. This heterogeneous copper catalyst exhibited higher activity than CuSO₄ and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Name: N-Phenylbenzo[d]thiazol-2-amine).

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. 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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

Synthesis and structure-activity relationships of novel lincomycin derivatives. Part 1. Newly generated antibacterial activities against Gram-positive bacteria with erm gene by C-7 modification was written by Wakiyama, Yoshinari;Kumura, Ko;Umemura, Eijiro;Ueda, Kazutaka;Masaki, Satomi;Kumura, Megumi;Fushimi, Hideki;Ajito, Keiichi. And the article was included in Journal of Antibiotics in 2016.Formula: C7H4N2O2S2 This article mentions the following:

The authors synthesized 7(S)-7-deoxy-7-arylthiolincomycin derivatives possessing a heterocyclic ring at the C-7 position via sulfur atom by either Mitsunobu reaction of 2,3,4-tris-O-(trimethylsiliyl)lincomycin or S_N2 reaction of 7-O-methanesulfonyl-2,3,4-tri-O-trimethylsiliyllincomycin. As a result, 7(S)-7-deoxy-7-arylthiolincomycin derivatives 7(S)-7-(6-aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin (16), 7(S)-7-(5-amino-1,3,4-thiadiazol-2-ylthio)-7-deoxylincomycin (21) and 7(S)-7-deoxy-7-(5-phenyl-1,3,4-thiadiazol-2-ylthio)lincomycin (27) exhibited antibacterial activities against respiratory infection-related Gram-pos. bacteria with erm gene, although clindamycin did not have any activities against those pathogens. Furthermore, 7(S)-configuration of lincomycin derivatives was found to be necessary for enhancing antibacterial activities from the comparison results of configurations of 16 (S-configuration) and 7(R)-7-(6-Aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin (30) (R-configuration) at the 7-position. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Formula: 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. 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.Formula: C7H4N2O2S2

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

Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities was written by Markey, Christine M.;Alward, Abdo;Weller, Paul E.;Marnett, Lawrence J.. And the article was included in Journal of Biological Chemistry in 1987.HPLC of Formula: 6318-74-7 This article mentions the following:

The peroxidase activity of prostaglandin H (PGH) synthase catalyzes reduction of 5-phenyl-4-pentenyl hydroperoxide to 5-phenyl-4-pentenyl alc. with a turnover number of ∼8000 mol of 5-phenyl-4-pentenyl hydroperoxide/mol of enzyme/min. The kinetics and products of reaction establish PGH synthase as a classical heme peroxidase with catalytic efficiency similar to horseradish peroxidase. This suggests that the protein of PGH synthase evolved to facilitate peroxide heterolysis by the heme prosthetic group. Comparison of an extensive series of phenols, aromatic amines, β-carbonyls, naturally occurring compounds, and nonsteroidal anti-inflammatory drugs indicates that considerable differences exist in their ability to act as reducing substrates. No correlation is observed between the ability of compounds to support peroxidatic hydroperoxide reduction and to inhibit cyclooxygenase. In addition, the resolved enantiomers of MK-410 and etodolac exhibit dramatic enantiospecific differences in their ability to inhibit cyclooxygenase but are equally potent as peroxidase-reducing substrates. This suggests that there are significant differences in the orientation of compounds at cyclooxygenase inhibitory sites and the peroxidase oxidation site(s). Comparison of 5-phenyl-4-pentenyl hydroperoxide reduction by PGH synthase and horseradish peroxidase reveals considerable differences in reducing substrate specificity. Both the cyclooxygenase and peroxidase activities of PGH synthase inactivate in the presence of low micromolar amounts of hydroperoxides and arachidonic acid. PGH synthase was most sensitive to arachidonic acid, which exhibited a concentration for 50% inhibition (I₅₀) of 0.6 μM in the absence of all protective agents. Inactivation by hydroperoxides requires peroxidase turnover and can be prevented by reducing substrates. The I₅₀ values for inactivation by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid are 4.0 and 92 μM, resp., in the absence and presence of 500 μM phenol, a moderately good reducing substrate. The ability of compounds to protect against hydroperoxide-induced inactivation correlates directly with their ability to act as reducing substrates. Hydroquinone, an excellent reducing substrate, protected against hydroperoxide-induced inactivation when present in <3-fold molar excess over hydroperoxide. The presence of a highly efficient hydroperoxide-reducing activity appears absolutely essential for protection of the cyclooxygenase capacity of PGH synthase. The peroxidase activity is, therefore, a twin-edged sword, responsible for and protective against hydroperoxide-dependent inactivation of PGH synthase. As such, it may constitute an important target for pharmacol. modulation of eicosanoid biosynthesis. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7HPLC of Formula: 6318-74-7).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.HPLC of Formula: 6318-74-7

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

Synthesis of N-substituted-2-aminobenzothiazoles using nano copper oxide as a recyclable catalyst under ligand-free conditions, in reusable PEG-400 medium was written by Gaddam, Satish;Kasireddy, Harshavardhan Reddy;Konkala, Karnakar;Katla, Ramesh;Durga, Nageswar Yadavalli Venkata. And the article was included in Chinese Chemical Letters in 2014.COA of Formula: C13H10N2S This article mentions the following:

A simple and practical method for the synthesis of 2-arylaminobenzothiazoles via a cross-coupling reaction of 2-iodoanilines with isothiocyanates is envisaged using nano copper oxide as a recyclable catalyst and Cs₂CO₃ as a base in PEG-400, as a bio-degradable, reusable, inexpensive and non-toxic reaction medium, under ligand-free conditions. The present tandem process underlines environmental acceptability to access a wide range of N-substituted-2-aminobenzothiazoles in good to excellent yields. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: 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. 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.COA of Formula: C13H10N2S

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

Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles was written by Zhu, Yan-Qiu;Zhang, Rui;Sang, Wei;Wang, Hua-Jing;Wu, Yuan;Yu, Bao-Yi;Zhang, Jun-Chao;Cheng, Hua;Chen, Cheng. And the article was included in Organic Chemistry Frontiers in 2020.Electric Literature of C13H10N2S This article mentions the following:

Herein, a wide range of mono- and di-arylated products were efficiently prepared from C-N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds I and II were further confirmed by X-ray crystallog. It was noteworthy that the di-arylated products, denoted as di(benzothiazolyl)amines, are new chem. entities which have not yet been reported. Moreover, the ligand-controlled protocol was extended to the synthesis of target mols. bearing a di-Ph ether or di-Ph amine scaffold. Several compounds exhibited good inhibitory activity against succinate-cytochrome c reductase (SCR), which revealed the practical application of this protocol. Notably, selective mono- and di-arylation could be switched simply by varying the ligand from Xantphos to a pyridine-functionalized N-heterocyclic carbene (NHC) ligand, and further investigations were carried out to elucidate the possible reason for this new finding. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Electric Literature of C13H10N2S).

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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Electric Literature of C13H10N2S

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