Month: February 2023

Heteroaromatic N-oxide. X. Synthesis and reactions of benzothiazole 3-oxide was written by Takahashi, Shiro;Hashimoto, Shinichiro;Kano, Hideo. And the article was included in Chemical & Pharmaceutical Bulletin in 1970.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Benzothiazole 3-oxide (I) was synthesized from its 2-Me derivative, via the corresponding aldoxime, carbonitrile, imido ester and carboxylic acid. The reactions of I: deoxygenation, reactions with various nucleophilic agents (tosyl chloride, Ac2O, PhMgBr, NaHSO3, N2H4.H2O and KCN-BzCl) involving some 1,3-dipolarophiles (benzyne, PhNCO and tetracyanoethylene), and quaternizations were investigated and compared with those of the corresponding imidazole N-oxide. 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 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation was written by Liao, Jennie;Guan, Weiye;Boscoe, Brian P.;Tucker, Joseph W.;Tomlin, John W.;Garnsey, Michelle R.;Watson, Mary P.. And the article was included in Organic Letters in 2018.Related Products of 55661-33-1 This article mentions the following:

A nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)arylmethanes, e.g., I. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

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.Related Products of 55661-33-1

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

Thiazole based novel functional colorants: Synthesis, characterization and nonlinear optical studies using picosecond Z-scan technique was written by Singh, Balvant Shyam;Lobo, Hyacintha Rennet;Krishna Podagatlapalli, G.;Venugopal Rao, S.;Shankarling, Ganapati Subray. And the article was included in Optical Materials (Amsterdam, Netherlands) in 2013.Synthetic Route of C15H12N2S This article mentions the following:

Organic push-pull chromophoric system containing thiazole Schiff bases were synthesized from aminothiazole intermediate. These novel chromophores possessed excellent thermal and optical properties with complete transparency in the visible spectral region. Thermogravimetric anal. revealed that all dyes were thermally stable at temperatures above 300 °C. The third-order nonlinear optical studies, performed using the Z-scan technique with ∼2 ps pulses, revealed excellent three photon absorption coefficients/cross-sections combined with reasonably high values of nonlinear refractive index (n₂). The solute n₂ was of opposite sign compared to that of solvents. To the best of our knowledge, this is the first report of three-photon absorption studies in Schiff base compounds In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Synthetic Route 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Synthetic Route of C15H12N2S

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

Reactions of new nitroethane derivatives; formation of new 1,5-benzothiazepines and benzothiazoles III was written by Bercin, Erdogan;Uysal-Gokce, Mehtap;Noyanalpan, Ningur. And the article was included in Journal of Faculty of Pharmacy of Gazi University in 1996.SDS of cas: 1843-21-6 This article mentions the following:

The reactions of [(aminophenyl)thio]phenylnitroethane derivatives, 2-NH₂C₆H₄SCH(CH₂NO₂)C₆H₄R (2; R = H, Me) with isothiocyanates and benzaldehydes were studied. The reaction of 2 with isothiocyanates, R¹NCS (R¹ = Ph, 4-ClC₆H₄) gave 2-anilinobenzothiazoles I. Depending on the reaction temperature, 2 reacted with benzaldehydes (4-R¹C₆H₄CHO, R¹ = H, Cl, OMe, OEt) to give either 2-phenylbenzothiazole derivative II or 1,5-benzothiazepines III (R = H, Me, R¹ = H). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 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. 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: 1843-21-6

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

Nickel-Catalyzed C-H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules was written by Yamamoto, Takuya;Muto, Kei;Komiyama, Masato;Canivet, Jerome;Yamaguchi, Jun-Ichiro;Itami, Ken-Ichiro. And the article was included in Chemistry – A European Journal in 2011.Category: thiazole This article mentions the following:

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. It has been established that Ni(OAc)₂/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)₂/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, a new protocol was discovered for the present coupling using Mg(OtBu)₂ as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodol. has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

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. 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

Combinatorial Approach to N-Substituted Amino-Cyclitol Libraries by Solution-Phase Parallel Synthesis and Preliminary Evaluation as Glucocerebrosidase Inhibitors was written by Serrano, Pedro;Casas, Josefina;Zucco, Martine;Emeric, Gilbert;Egido-Gabas, Meritxell;Llebaria, Amadeu;Delgado, Antonio. And the article was included in Journal of Combinatorial Chemistry in 2007.Related Products of 69812-29-9 This article mentions the following:

Libraries of N-substituted amino-cyclitol derivatives of the scyllo and racemic chiro series by means of parallel solution-phase methodol. with the help of robotic technol. are described. Chem. diversity has been introduced by reaction of selected scaffolds with a set of aldehydes, acyl chlorides, sulfonyl chlorides, chloroformates, and amines to afford the corresponding amines, amides, sulfonamides, carbamates and ureas, resp. The optimized methodol. has proven excellent, in terms of overall purity of the resulting libraries, for the production of amides. Sulfonamides and carbamates have been obtained in slightly lower purity, while amines afforded modest results. Selected library members have been evaluated as inhibitors of recombinant glucocerebrosidase with K_i values ranging in the low micromolar scale for the most active members. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Related Products of 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Related Products of 69812-29-9

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

Biologically active fused heterocycles from naturally occurring quinones-Part-II: synthesis of 3-substituted-9-hydroxy-10-undecyl-benzo[2′,3′,:4,5]thiazolo[2,3-b]benzimidazole-8,11-diones and their antimicrobial activity was written by Rani, T. Usha;Rao, M.S.;Reddy, V. M.. And the article was included in Indian Journal of Heterocyclic Chemistry in 1997.Application of 58759-63-0 This article mentions the following:

Title compounds were prepared by condensation of 2-mercaptobenzimidazoles with bromoembelin and then converted into their acetyl, reduced acetyl, phenazine and N-acetylphenazine derivatives The compounds have been characterized by their anal. and spectral properties. Some of these compounds exhibit moderate antimicrobial activity. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Application of 58759-63-0).

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. 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.Application of 58759-63-0

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

Syntheses of new sulfonamides. VIII. Syntheses of new hypoglycemic sulfonamides related to 2-sulfanilamido-5- isopropyl-1,3,4-thiadiazole was written by Takatori, Kichitaro;Yamada, Yasuo;Asano, Shingo. And the article was included in Yakugaku Zasshi in 1959.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

The following RSO₂Cl are prepared (R and m.p. given): p-AcNHC₆H₄, 149°; p-MeAcNC₆H₄, 126°; 3,4-Me(AcNH)C₆H₃, 159°; 4,3-Me(AcNH)C₆H₃, 142°; p-O₂NC₆H₄, 80°; Ph, 14.5°; p-MeC₆H₄, 69°; 3,6-Me₂C₆H₃, 24-6°; p-EtOCO₂C₆H₄, 71°, 6,2-EtOCO₂C₁₀H₆, 118°; p-FC₆H₄, 53°; p-BrC₆H₄, 76°; 2-acetamido-4-methyl-5-thiazolyl, 157° (decomposition). NH₂CSNHNH₂ (1 mole) and 2 moles corresponding acid chloride refluxed 1 hr., the product at 80-90° extracted with dilute HCl and made alk. with NH₄OH or Na₂CO₃ gave 2-amino-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 235°; Et, 196°; Pr, 203°; iso-Pr, 187°; Bu, 196°; iso-Bu, 229°; Am, 195°; undecyl, 115°. 2-Amino-5-isopropyl-1,3,4-thiadiazole (I) (0.1 mole) in 140 ml. C₅H₅N was heated 1 hr. at 100° with 0.1 mole p-AcNHC₆H₄SO₂Cl, the C₅H₅N removed and the residue treated with 100 ml. 10% HCl to give 28.4 g. 2-(p-AcNHC₆H₄SO₂NH) analog (II) of I, m. 183-4° (EtOH). II (28.4 g.) in 200 ml. 10% NaOH heated 1 hr. at 100° and the product recrystallized (H₂O) gave 15.4 g.2-(p-H₂NC₆H₄SO₂NH) analog of I, m. 195°. Similarly are prepared 2-RSO₂NH analogs of I (R and m.p. given): p-MeNHC₆H₄, 141°; 3,4-Me(H₂N)C₆H₃, 175°; 4,3-Me(H₂N)C₆H₃, 163°; p-HOC₆H₄, 100°; p-MeC₆H₄ (monohydrate), 93° (decomposition); 2,5-Me₂C₆H₃, 120°; p-O₂NC₆H₄, 172°; p-FC₆H₄, 97-9°; p-ClC₆H₄, 133°; p-BrC₆H₄, 142°; Ph, 125°; 2-acetamido-4-methyl-5-thiazolyl, 255-7° (decomposition). Condensation of equimolar amounts of 2-amino-5-alkyl-1,3,4-thiadiazole and p-MeC₆H₄SO₂Cl in C₅H₅N yielded 2-(p-toluenesulfonamido)-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 198°; Et, 130°; Pr, 139°; iso-Pr, 108°; Bu, 114°; Me₂CHCH₂, 175°; Am, 128°; Me(CH₂)₁₀, 92°. The sulfonamides of this series which have the power to reduce blood sugar level are generally soluble in dilute alk. carbonate, similar to N-acylated arenesulfonamides. This property was utilized for their purification. 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 thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship was written by Buchholz, Mirko;Heiser, Ulrich;Schilling, Stephan;Niestroj, Andre J.;Zunkel, Katrin;Demuth, Hans-Ulrich. And the article was included in Journal of Medicinal Chemistry in 2006.Computed Properties of C9H10N2O2S This article mentions the following:

The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the mols., which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Computed Properties of 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. 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.Computed Properties of C9H10N2O2S

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

Complexation of copper(II), cobalt(II), nickel(II) and chromium(III) with 2-hydroxy-, 2-hydrazo- and 2-phenylaminobenzothiazole in water-ethanol solutions was written by Manolov, S.;Davarski, K.;Auatai, I.. And the article was included in Koordinatsionnaya Khimiya in 1987.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Ligand acid dissociation and metal complexation constants were determined pH-metrically at 293 K in flowing N atm. Stability constants (log β) for 1:1 and 1:2 metal:ligand complexes decrease in the order Cr (III) > Cu(II) > Ni(II) ∼ Co(II). 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. 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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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