Month: February 2023

Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary Amines and N₁,C₅-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl Alcohols was written by Donthiri, Ramachandra Reddy;Pappula, Venkatanarayana;Chandra Mohan, Darapaneni;Gaywala, Hiren H.;Adimurthy, Subbarayappa. And the article was included in Journal of Organic Chemistry in 2013.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. E.g., in presence of NaOH in toluene, N-alkylation of 2-aminobenzothiazole with 4-ClC₆H₄CH₂OH gave 93% I. With 1 equiv of NaOH, N₁,C₅-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N₁,C₅-dialkylated products through hydride ion transformation from alc. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 4,5-Diphenylthiazol-2-amine

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

CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide was written by Li, Jiaojiao;Zhang, Yihua;Jiang, Yongwen;Ma, Dawei. And the article was included in Tetrahedron Letters in 2012.Category: thiazole This article mentions the following:

A copper-catalyzed procedure was developed for assembling benzothiazolones from Et 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Category: thiazole).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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.Category: thiazole

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

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles was written by Wimmer, Laurin;Parmentier, Michael;Riss, Bernard;Kapferer, Tobias;Ye, Chao;Li, Lei;Kim, Hongyong;Li, Jialiang. And the article was included in Synthesis in 2018.Synthetic Route of C7H3BrClNS This article mentions the following:

The substituted 2-mercaptobenzothiazoles were prepared (by reaction of 2-haloanilines and potassium o-Et carbonodithioate) and underwent chlorination using sulfuryl chloride/water so as to yield 2-chlorobenzothiazoles such as I [X = C, N; R = H, 6-Me, 7-Cl, etc.]. This straightforward and widely used reaction was impeded due to the poor reproducibility and low reaction yields. In this protocol, it was reported that the simple addition of water to the reaction lead to remarkable improvements in reaction efficiency because of the formation of acid through partial hydrolysis of sulfuryl chloride. The observations of improved yields were also obtained in the presence of some anhydrous acidic additives, but the simple combination of sulfuryl chloride and water reproducibly provided excellent yields for a range of chlorinated products I. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Synthetic Route of C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.Synthetic Route of C7H3BrClNS

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

Synthesis and biological evaluation of alkyl, alkoxy, alkylthio, or amino-substituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones was written by Inoue, Hirozumi;Konda, Mikihiko;Hashiyama, Tomiki;Otsuka, Hisao;Watanabe, Akishige;Gaino, Mitsunori;Takahashi, Kaoru;Date, Tadamasa;Okamura, Kimio;Takeda, Mikio;Narita, Hiroshi;Murata, Sakae;Odawara, Akio;Sasaki, Haruhiko;Nagao, Taku. And the article was included in Chemical & Pharmaceutical Bulletin in 1997.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones,e.g., I (R¹ = 6-, 7-, 8-Me, 7-CF₃, 7-OMe, etc., R² = OMe, OCF₃, Me, etc.), substituted with an alkyl, alkoxy, alkylthio, hydroxy, or amino group on the fused benzene ring of the 1,5-benzothiazepine skeleton were synthesized and their vasodilating, antihypertensive, and platelet aggregation-inhibitory activities were investigated. (-)-Cis-3-Acetoxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-8-methyl-2-(4-m ethylphenyl)-1,5-benzothiazepin-4(5H)-one was selected for further studies as a potent inhibitor of platelet aggregation. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

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 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.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Applications of Snyder’s theory on linear adsorption chromatography to heterocyclic compounds. I. Influence of the polar and steric effects of various substituents on the adsorption energy of thiazoles on alumina was written by Vernin, Gaston;Vernin, G. Mrs.. And the article was included in Journal of Chromatography in 1970.HPLC of Formula: 6318-74-7 This article mentions the following:

The Snyder theory of linear adsorption chromatog., that was applied to on e hundred thiazole derivatives, made it possible to determine exptl. the adsorption energies of the compounds and to compare these with the adsorption energies calculated by means of fixed tables. In a study on thiazoles containing one or two alkyl groups, this comparison made it possible to determine the variations in adsorption energy of the N atom of the ring due to the polarization effects and to the steric effects induced by the alkyl groups and to relate these effects to the constant relations which exist between the polarization and steric effects of the substituents. A similar investigation was made on 4-aryl thiazoles with various substituents in the 2-position. In this case variations in the adsorption energy of the mols. due to the polarization effects of the groups substituted para to the phenyl group with respect to the substituents in the 2-position were studied, and the mutual electronic interactions between the various groups were determined 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. 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 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.HPLC of Formula: 6318-74-7

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

Some thiazoles and oxazoles was written by Bachstez, Marcel. And the article was included in Berichte der Deutschen Chemischen Gesellschaft in 1914.Reference of 1826-13-7 This article mentions the following:

Rüdenburg, C. A. 8, 686. From 2 g. each of BzNHCH₂CH(OEt)₂ and P₂S₅, heated on the H₂O bath till the foaming ceases, is obtained 0.3 g. 2-phenylthiazole (Hubacher, Ann. 269, 234) . 1 g. HCONHCH₂Bz (a), m. 81-2° (Pictet and Gams, C. A. 4, 3222, give 70-1°), heated 10 min. with 1.5 g. P₂S₅, gives 0.6 g. 5-phenylthiazole, iridescent leaflets, m. 45-6°; hydrochloride, hygroscopic needles, decompose by much H₂O or by warming; chloroplatinate, yellow precipitate, decompose 281-2°; chloroaurate, yellow-red rhombic plates, sinters 170°, m. 185°, decompose about 223°; chromate, ocher-yellow rodlets and needles from 10% HCl, m. 108-9° (decompose); picrate, light yellow needles, m. 138-9° (decompose). 5-Phenyloxazole, from (a) and PCl₅ after 10 min. on the H₂O bath, m. 41-2°; hydrochloride, hygroscopic; chloroaurate, long orange needles, m. 149-50°; chloroplatinate, long light yellow needles, does not decompose 275°. α-Acetaminopropiophenone (b), obtained in 0.8 g. yield from 1 g. BzCHMeNH₂.HCl in 15 cc. ice H₂O and 2 cc. Ac₂O, rhombic pyramids from C₆H₆, m. 90-1°; with 2 parts PCl₅ 10 min. on the H₂O bath it gives 2,4-dimethyl-5-phenyloxazole, m. 51-2°; hydrochloride, hygroscopic rodlets, slowly volatilizes in vacuo, decompose by H₂O; chromate, orange needles, m. 100-1° (foaming); chloroplatinate, long yellow-red needles with 2 H₂O, m. 240° (foaming); chloroaurate, short rodlets; picrate, felted needles, m. 171-2.5°. 2,4-Dimethyl-5-phenylthiazole, obtained in 50% yield from equal parts of (b) and P₂S₄ heated 10 min. to 140°, b₇₆₈ 270-1°; hydrochloride, hygroscopic rodlets, decompose by much H₂O; chloroplatinate, long yellow-red needles with 2 H₂O, sinters 235°, m. 239-40° (foaming); chloroaurate, needles; chromate, fleshred needles, m. 105-6°; picrate, felted needles, m. 155.5-6.5°. Benzaminoisobutyrophenone, from BzCMe₂NH₂.HCl and BzCl in NaOH, needles from 50% alc., m. 61°, does not react with PCl₅ alone or in POCl₃. ω-Ethyloxalylaminoacetophenone, BzCH₂NHCOCO₂Et, from BzCH₂NH₂.HCl in cold H₂O treated with NaHCO₃ and ClOCCO₂Et, striated prisms from H₂O, m. 96-7°; the yield was so small that its reaction with PCl₄ could not be tried out. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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.Reference of 1826-13-7

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

Carbon-13 NMR studies of variously substituted phenylthiazoles. Substituent effects, conformational study and prototropic tautomerism was written by Faure, Robert;Assaf, Abdelghani;Vincent, Emile Jean;Aune, Jean Pierre. And the article was included in Journal de Chimie Physique et de Physico-Chimie Biologique in 1978.Synthetic Route of C9H7NS This article mentions the following:

The ¹³C NMR of I (R = H, 2-Ph, 4-Ph, 5-Ph) was examined and the dihedral angle between the Ph and thiazole ring systems determined; comparison of other heterocyclic ring systems with I indicated that the perturbation observed on Ph substitution decreased with the increase in heteroatom electronegativity. Steric interactions were observed in 4,5-disubstituted phenylthiazoles and the substituent effects were nonadditive; additivity was observed in 2,4- and 2,5-disubstituted phenylthiazoles. The protonation of I and the tautomerization of II (R¹ = H, Ph; R² = NH₂, SH, OH) was also discussed. 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. 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 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.Synthetic Route of C9H7NS

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

Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors was written by Han, Yongxin;Giroux, Andre;Colucci, John;Bayly, Christopher I.;Mckay, Daniel J.;Roy, Sophie;Xanthoudakis, Steve;Vaillancourt, John;Rasper, Dita M.;Tam, John;Tawa, Paul;Nicholson, Donald W.;Zamboni, Robert J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.COA of Formula: C4H6N2S This article mentions the following:

The iterative process for the discovery of a series of pyrazinone mono-amides as potent, selective and reversible non-peptide caspase-3 inhibitors (e.g., M826 and M867) is reported. The studied compounds were prepared according to modified literature procedure from ethylaminobutyrate hydrochloride via intermediate acids (e. g., I), which were synthesized using Dess-Martin periodinane oxidation Treating of coupled to the resin in the presence of Hunig’s base intermediate acids I with 90% TFA in water gave the desired inhibitors (e. g. II). These compounds were screened directly, without further purification, against four representative recombinant human caspases, as well as in the NT2 cell against camptothecin induced apoptosis. 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. 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.COA of Formula: C4H6N2S

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

Fungicidal activities and mass spectral studies of some Schiff bases derived from p-hydroxybenzaldehyde and their derivatives was written by Dash, B.;Mahapatra, P. K.;Panda, D.;Pattnaik, J. M. Mrs.. And the article was included in Journal of the Indian Chemical Society in 1984.Electric Literature of C15H12N2S This article mentions the following:

A new series of Schiff bases were prepared Condensation of 2-aminothiazoles and -benzothiazoles with p-HOC₆H₄CHO gave I [R = H, R¹ = aryl, R² = H, aryl, R²R² = (un)substituted CH:CHCH:CH]. Chloroacetylation of I (R = H) followed by substitution with morpholine and piperidine gave I (R = morpholinoacetyl, piperidinoacetyl). Cycloaddition of I (R = H) with HSCH₂CO₂H yielded thiazolidinone derivatives II. I and II have satisfactory fungicidal activity against Curvularia at 500 ppm. The mass spectra of I (R = H) were discussed. 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. 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.Electric Literature of C15H12N2S

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

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling was written by Liu, Chengwei;Ji, Chong-Lei;Zhou, Tongliang;Hong, Xin;Szostak, Michal. And the article was included in Angewandte Chemie, International Edition in 2021.SDS of cas: 1826-13-7 This article mentions the following:

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chem. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling [e.g., benzoxazole + benzoic acid → 2-phenylbenzoxazole (92%)]. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetalation of the copper-aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation. 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 1826-13-7

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