Day: January 4, 2023

Benzothiazole. I. Nitration and bromination of 2-chlorobenzothiazole was written by Colonna, Martino. And the article was included in Pubbl. ist. chim. univ. Bologna in 1943.HPLC of Formula: 80945-86-4 This article mentions the following:

According to the hypothesis of Bonino (C.A. 34, 323.6) direct “cationoid” substitution (halogenation, nitration, etc.) of benzothiazole (I) should be directed toward the positions of the H atoms statistically pos., i. e., 4 or 6, while “anionoid” substitution (e. g., with NaNH₂, NH₂OH, etc.) should be directed toward the positions of the H atom statistically neg., i. e., 2. In order to test these predictions, 2-chlorobenzothiazole (II) was prepared (cf. Ger. pat. 516,996 (C.A. 25, 3015)) by the action of PCl₅ and POCl₃ on 2-mercaptobenzothiazole (III). II dissolved in concentrated H₂SO₄, treated with EtNO₃ at 0°, gives a crystalline precipitate of 2-chloro-6-nitrobenzothiazole (IV), m. 192°, which at 140° (under pressure) with alc. NH₃ gives 2-amino-6-nitrobenzothiazole (V), yellow, m. 245° (alc.), identical with the compound obtained by treating p-nitro-aniline with NH₄CNS (cf. Kauffmann, C.A. 29, 2660.1). IV with Br in CHCl₃ gives 2-chloro-6-bromobenzothiazole, white, m. 100-1°, and the same compound is obtained by treating the diazo derivative of IV with Cu₂Br₂. The structure of I according to Bonino shows the pyridine-like character of the N atom, and the strictly aromatic character of the benzene nucleus; however, in this nucleus the tricentered bond is fixed, while in other nuclei it is of an oscillating type, as in the equilibrium of quinoline: (VI)⇌ (VII). In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4HPLC of Formula: 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.HPLC of Formula: 80945-86-4

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

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C-H sulfurization: a new route to 2-aminobenzothiazoles was written by Yao, Guangkai;Wang, Bing-Feng;Yang, Shuai;Zhang, Zhi-Xiang;Xu, Han-Hong;Tang, Ri-Yuan. And the article was included in RSC Advances in 2019.Synthetic Route of C13H10N2S This article mentions the following:

DMSO was found to activate arylisothiocyanates for self-nucleophilic addition A subsequent intramol. C-H sulfurization catalyzed by PdBr₂ enable accessed to a wide range of 2-aminobenzothiazole derivatives in moderate to good yields. This is the first example of a DMSO-mediated Pd-catalyzed synthesis of 2-aminobenzothiazoles through cyclization/C-H sulfurization of two isothiocyanates. 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. 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.Synthetic Route of C13H10N2S

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

Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines was written by McLean, Liam A.;Ashford, Matthew W.;Fyfe, James W. B.;Slawin, Alexandra M. Z.;Leach, Andrew G.;Watson, Allan J. B.. And the article was included in Chemistry – A European Journal in 2022.Category: thiazole This article mentions the following:

A method for the synthesis of chiral vicinal chloroamines RCH(Cl)CH₂NHR¹ [R = 2-quinolyl, quinazolin-2-yl, 1,3-benzothiazol-2-yl, etc.; R¹ = Ph, 4-MeC₆H₄, benzothiophen-5-yl, etc.] via asym. protonation of catalytically generated prochiral chloroenamines using chiral Bronsted acids was reported. The process was highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations The utility of the method showed as an approach to the synthesis of a broad range of heterocycle-substituted aziridines I [R² = 2-quinolyl, quinoxalin-2-yl, 5-cyano-2-pyridyl, etc.; Ar = Ph, 4-MeOC₆H₄, 3-BrC₆H₄, etc.] by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines II [R³ = 4-tert-butoxycarbonylpiperazin-1-yl, morpholino, thiomorpholino]. 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. 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.Category: thiazole

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

Synthesis of 2-amino-4,5-diphenylthiazoles was written by Liu, Wei-wei;Huo, Yun-feng;Zhang, Qiang;Li, Qu-xiang;Wu, Jun;Fang, Qun. And the article was included in Huaxue Shiji in 2014.Electric Literature of C15H12N2S This article mentions the following:

Five 2-hydroxy-1,2-diarylenthanones were synthesized by benzoin condensation with aromatic aldehydes as raw material and the reaction conditions were investigated. The optimized conditions are: n(catalyst) = 20 mol%, n(NaOH) = 10 mol%, and V(H₂O) : V(C₂H₅OH) = 1 : 3 as reagent. The 2-amino-4,5-diarylthiazoles I(R = H, 4-Me, 4-MeO, 2-MeO, 4-Cl, 2-Cl) were synthesized from 2-hydroxy-1,2-diary lenthanones by a two-step reaction of chlorination and cyclization. The structures of were confirmed by IR, ¹HNMR and HRMS. 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. 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.Electric Literature of C15H12N2S

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

Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles was written by Dondoni, Alessandro;Merchan, Francisco L.;Merino, Pedro;Rojo, Isabel;Tejero, Tomas. And the article was included in Synthesis in 1996.Formula: C4H6N2S This article mentions the following:

A method for the enantioselective synthesis of (aminoalkyl)thiazoles I (R = PhCH₂, allyl,cyclohexylmethyl, Me, 4-ClC₆H₄CH₂) via stereoselective alkylation of the imines of (+)-(R)-camphor or (-)-(1S,2S,5S)-2-hydroxy-3-pinanone and 2-thiazolemethanamine is described. Compounds I served as α-amino aldehyde precursors via thiazolyl-to-formyl conversion. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Formula: C4H6N2S

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

CP6679, a new injectable cephalosporin. Part 1: Synthesis and structure-activity relationships was written by Tsushima, M.;Iwamatsu, K.;Umemura, E.;Kudo, T.;Sato, Y.;Shiokawa, S.;Takizawa, H.;Kano, Y.;Kobayashi, K.;Ida, T.;Tamura, A.;Atsumi, K.. And the article was included in Bioorganic & Medicinal Chemistry in 2000.Recommanded Product: 55661-33-1 This article mentions the following:

A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo[5,1-b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (I) and its analogs showed potent antibacterial activities against Gram-pos. and Gram-neg. bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). I showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 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). 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.Recommanded Product: 55661-33-1

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

Suzuki cross-coupling reaction of aryl and heterocyclic bromides and aromatic polybromides on a Pd(II)-hydrotalcite catalyst was written by Mora, Manuel;Jimenez-Sanchidrian, Cesar;Ruiz, Jose Rafael. And the article was included in Applied Organometallic Chemistry in 2008.Formula: C9H7NS This article mentions the following:

The Suzuki cross-coupling reaction of various bromine-containing substrates and phenylboronic acid in toluene at 90 °C on a Pd(AcO)₂Py₂ catalyst supported on an Mg-Al hydrotalcite, using K₂CO₃ as the base, was studied. The conversion and selectivity results obtained for many of the substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The reactions of aryl polybromides and phenylboronic acid gave the corresponding polyaromatic compounds in variable yields depending on the particular substrate. Arylation occurred in a consecutive manner by substitution of the different Br atoms. ICP-MS measurements of the palladium content of the catalyst performed prior to and after the reaction revealed that part of the metal is incorporated into the bulk solution; therefore, the catalytic process is not purely heterogeneous. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Formula: 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Formula: C9H7NS

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

Decreased sulfotransferase gene expression in DPT-induced polycystic kidney was written by Tanaka, Yoshihiko. And the article was included in Osaka-shi Igakkai Zasshi in 2001.Safety of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Polycystic kidney is induced by feeding 1% 2-amino-4,5-diphenylthiazole (DPT) to rats. The alteration of gene expressions on the fourth day in this model was investigated with differential display method (DD). Among the bands which showed different intensities on DD, the decreased expression was confirmed by Northern blot anal. Using this PCR product as a probe, mouse kidney cDNA library was screened. Cloned cDNA of 1482 bp contained open reading frame encoding 296 amino acids, which was 94.3% identical to rat SULT1C2 sulfotransferase and was thought to be an isoform of SULT1C2. Mouse SULT1C2 mRNA was abundant in kidneys and stomachs of normal mice. The expression of SULT1C2 mRNA was decreased the day after DPT feeding and was still low after 2 wk. Although the physiol. substrate and function of SULT1C2 have yet to be elucidated, it may be involved with the sulfation of proteoglycans composing the tubular basement membranes. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Safety of 4,5-Diphenylthiazol-2-amine).

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

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

The efficient palladium-catalyzed selective synthesis of benzenesulfonic acids was written by Jagadeesh, Rajenahally V.;Sandhya, Y. Sree;Karthikeyan, P.;Reddy, S. Sudhakar;Reddy, P. Pradeep Kumar;Kumar, M. Viniod;Charan, K. T. Prabhu;Narender, R.;Bhagat, P. R.. And the article was included in Synthetic Communications in 2011.Formula: C8H5NO2S This article mentions the following:

Palladium-catalyzed synthetic methodol. was developed for the synthesis of 2-aminobenzenesulfonic acids from benzothiazoles in good to excellent yields using chloramine-B in alk. (pH 12) acetonitrile-water (1:1) at 80 °C. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Formula: C8H5NO2S).

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).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Formula: C8H5NO2S

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

Synthesis of 4-substituted imino-4H-benzo[d][1,3] thiazin-2-amines via palladium-catalysed isocyanide insertion in 2-bromophenylthioureas was written by Pandey, Garima;Bhowmik, Subhendu;Batra, Sanjay. And the article was included in RSC Advances in 2014.SDS of cas: 1843-21-6 This article mentions the following:

The palladium-catalyzed isocyanide insertion in 2-bromophenylthioureas resulted in the formation of 4-substituted imino-4H-benzo[d][1,3]thiazin-2-amines, e.g., I, via C-S cross coupling reaction of the intermediate imidoylpalladium species. The investigations into the substrate scope revealed that reactions of cyclohexyl isocyanide were successful with aromatic as well as aliphatic thioureas, whereas reactions of all other isocyanides (except Et 2-isocyanoacetate) were successful with aromatic thioureas only. 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. 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.SDS of cas: 1843-21-6

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