Category: 1843-21-6

Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles was written by Duangkamol, Chuthamat;Phakhodee, Wong;Pattarawarapan, Mookda. And the article was included in Synthesis in 2020.Formula: C13H10N2S This article mentions the following:

A convenient method for the synthesis of amino-benzimidazoles/benzoxazoles/benzothiazoles I [R¹ = H, 5-Me, 5-Cl, etc.; R² = Ph, Bn, 4-BrC₆H₄, etc.; X = NCH₂C₆H₄Me, O, S, etc.] was developed via potassium periodate-mediated oxidative cyclodesulfurization of isothiocyanates with ortho-substituted anilines bearing N,N-, N,O-, and N,S-bis-nucleophiles, followed by an intramol. cyclization of the in situ generated monothioureas in good to excellent yields. The protocol could accommodate various substituents on both substrates while allowing more efficient, greener and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives II [R³ = H, 8-Me, 9-Me, 9-Cl] were also afforded in high yields in a single preparative step and chromatog.-free. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: 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 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.Formula: C13H10N2S

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

Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure-Activity Relationships was written by Shen, Qilong;Ogata, Tokutaro;Hartwig, John F.. And the article was included in Journal of the American Chemical Society in 2008.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The authors describe a systematic study of the scope and relation between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alkylphosphines for the amination of heteroaryl and aryl chlorides, bromides, and iodides. In the presence of this catalyst, aryl and heteroaryl chlorides, bromides, and iodides react with many primary amines in high yields with part-per-million quantities of palladium precursor and ligand. Many reactions of primary amines with both heteroaryl and aryl chlorides, bromides, and iodides occur to completion with 0.0005-0.05 mol % catalyst. A comparison of the reactivity of this catalyst for the coupling of primary amines at these loadings is made with catalysts generated from hindered monophosphines and carbenes, and these data illustrate the benefits of chelation. Studies on structural variants of the most active catalyst indicate that a rigid backbone in the bidentate structure, strong electron donation, and severe hindrance all contribute to its high reactivity. Thus, these complexes constitute a fourth-generation catalyst for the amination of aryl halides, whose activity complements catalysts based on monophosphines and carbenes. 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. 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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

Thiazole derivatives as vulcanization accelerators. I. Reaction of carbon disulfide, sulfur, and thiocarbanilide was written by Kimijima, Takuzo;Miyama, Shunichi. And the article was included in Kogyo Kagaku Zasshi in 1942.COA of Formula: C13H10N2S This article mentions the following:

A mixture of 231 g. thiocarbanilide, 67.5 g. S, and 83.6 g. CS₂ was heated in an autoclave at 180-260° for 6 hrs. to obtain mercaptobenzothiazole. The best temperature was 220°, at which the yield was 88%. At lower temperatures, anilidobenzothiazole was the chief product. The same was true when the mixture was heated at higher temperatures for a short time. When the reaction temperature was too high, benzothiazole was formed at the expense of mercaptobenzothiazole. 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 are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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

Oxidative coupling of formamides with β-dicarbonyl compounds and the synthesis of 2-aminobenzothiazole using Cu(II)-functionalized Fe₃O₄ nanoparticles was written by Azizi, Kobra;Karimi, Meghdad;Heydari, Akbar. And the article was included in Tetrahedron Letters in 2015.Application of 1843-21-6 This article mentions the following:

The Fe₃O₄@EDTA-Cu(II) nanoparticles catalyzed oxidative coupling of formamides with β-dicarbonyl compounds is developed using tert-Bu hydroperoxide as an oxidant. In general, the enol carbamates are synthesized in excellent yields (up to 92%) under the optimized reaction conditions. Fe₃O₄@EDTA-Cu(II) has the advantage of being magnetically recoverable. Also, we have established a highly efficient Fe₃O₄@EDTA-Cu(II)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates for the synthesis of 2-aminobenzothiazoles. 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). 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.Application of 1843-21-6

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

Acylation of 2-aminobenzothiazole and its 2- and 3-derivatives was written by Rozhkova, N. K.;Saprykina, V. A.. And the article was included in Uzbekskii Khimicheskii Zhurnal in 1975.Recommanded Product: 1843-21-6 This article mentions the following:

Pyrimidobenzothiazole I was obtained in 85% yield by acylation of II (R = R1 = H) with CH2:CHCOCl in dry Me2CO at room temperature II (R = Me, Ph, H, R1 = COCH:CH2, CO2Me, CO2Et) were obtained in 48-92% yields by acylation of II (R = Me, Ph, R1 = H) with R1COCl. Analogously obtained were 90-4% III (R = Me, Ph, R1 = COCH:CH2, CO2Me, CO2Et) by acylation of III (R1 = H) with R1COCl. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. 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: 1843-21-6

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

Esters of sulfonic acids. VI. Preparation and reactions of alkylisothiourea p-toluenesulfonates was written by Klamann, D.;Drahowzal, F.. And the article was included in Monatshefte fuer Chemie in 1952.Reference of 1843-21-6 This article mentions the following:

ROC₈H₁₇ (R = p-MeC₆H₄SO₂) (28.4 g.), refluxed 1 hr. with 7.6 g. thiourea in 80 cc. absolute alc., cooled to -20°, filtered, the mother liquor concentrated, the product crystalline and filtered, and the remaining solution treated with ether, gave a total of 98% practically pure octylpseudothiourea p-toluenesulfonate (I), m. 112-13°. When the alkylpseudothiourea salt (II) is not to be isolated, 96% alc. may be used; the alc. is distilled, and the residue heated to dryness (steam bath). ROMe (46.5 g.) and 19 g. thiourea in 20 cc. water, heated gently with stirring until the mixture was homogeneous, then heated to dryness, gave 99% Me derivative (III), m. 144-5°. The following II were prepared, [% yield of purified product and m.p. (from absolute alc. unless specified), given]: III, 93, 144-5°; Et (IV), 90, 125-6°; Bu, 87, 166°; iso-Bu, 88, 156-7°; hexyl, 87, 139.5-40.5° (from H₂O); I, 85, 112.5-13.5° (from (C₆H₆); dodecyl (1.5-hr. reaction time), 88, 102-3° (from C₆H₆); octadecyl (1.5-hr. reaction time), 88, 103.4-4.5°; PhCH₂, 80, 181.5-2.5°; cyclohexyl, 51, 169° (decomposition); 1,2-ethanedi (V) (0.5-hr. reaction time), 84, 269-79° (decomposition) (from H₂O); 1,6-hexanedi (VI), 84, 236-6.5° (from H₂O); ClCH₂CH₂, 34 (40% V.HCl as by-product), m. 141.5-2.5° (reaction time 15 min., 50% yield with 8% V). ROCH₂CH₂Cl with PhOH gives a trace of (CH₂OPh)₂, with PhSH 55% (CH₂SPh)₂. Thiourea and ROPh or the p-NO₂ derivative (0.1 mol. each), heated 6 hrs. in 100 cc. absolute alc. gave 97-8% recovery of ROPh. To stirred 38 g. RCl and 26 cc. EtOH was added (30 min., 12-17°) 32 cc. 25% NaOH and the mixture stirred 2 hrs. at 15-18°, neutralized with HCl, treated with 13 g. thiourea and warmed 1 hr. on a water bath, concentrated to dryness, and extracted with absolute alc., giving 83% IV, m. 125-6°. To 0.2 mol. III in 300 cc. H₂O, stirred at -2 to 3°, was added Cl, the solution turning green; after 100 min. the liquid product was extracted with ether, washed with 5% NaHSO₃ and H₂O, dried, concentrated, and distilled giving 75% MeSO₂Cl, b₉ 46-7°, n_D²⁰ 1.4505, 98.34% pure (Drahowzal and Klamann, C.A. 45, 10134d). Similarly the following sulfonyl chlorides were prepared (solid products were filtered, washed, dried, taken up in ether, filtered, and recrystallized), (% yield, b₉, and n_D²⁰ or m.p., and purity, resp., given): Et, 87, 55-5.5°, 1.4539, 98.51; Bu, 85, 80-1°, 1.4559, 98.64; hexyl, 85, 106.5-7°, 1.4585, 99.94; dodecyl, 87, m. 42-3°, 98.19; PhCH₂, 88, m. 91-2°, 97.23: 1,6-hexanedi, 80, m. 82-3°, 98.80; ClCH₂CH₂, 75, 81-2°, 1.4925, – (EtSO₂Br, 58, 73-4°, -, 95.31; EtSO₂NH₂, m. 59-60°). VI (23.2 g.) refluxed 2 hrs. with 9 g. KOH in 100 cc. H₂O, cooled, diluted with H₂O, acidified with dilute H₂SO₄, extracted with ether, and the extract washed, dried, concentrated, and distilled, gave 5.6 g. HS(CH₂)₆SH, b₁₂ 105.5-6°, n_D²⁰ 1.5106. Similarly the following mercaptans were prepared: 78% Et, b₇₅₄ 34.5°; 84% Bu, b₇₅₂ 97-8°; 86% octyl, b₂₀ 88.5°, n_D²⁰ 1.4541; and 24% cyclohexyl. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

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 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.Reference of 1843-21-6

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

Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization was written by Kadagathur, Manasa;Sigalapalli, Dilep Kumar;Patra, Sandip;Tangellamudi, Neelima D.. And the article was included in Synthetic Communications in 2021.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A novel approach has been developed to construct benzoxazoles and similar N- and S-containing heterocycles from their corresponding isothiocyanates and o-substituted anilines via cyclodesulfurization. The reaction was found to proceed via in situ formation of disubstituted thiourea, followed by intramol. cyclodesulfurization to yield the desired benzazole. Cyclodesulfurization was achieved by the application of safer and inexpensive oxidant, hydrogen peroxide (H₂O₂) under microwave irradiation In addition to the safe environmental footprints that hydrogen peroxide exhibits, the absence of any base or additive makes it a mild and green synthetic strategy. This method contributes to the field of metal- and base-free cyclodesulfurization, thereby aids the synthesis of pharmacol. potent heterocyclic scaffolds. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. 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.Quality Control of N-Phenylbenzo[d]thiazol-2-amine

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

Liquid chromatography-mass spectrometry for the identification of minor components in benzothiazole derivatives was written by Niessen, W. M. A.;McCarney, C. C.;Moult, P. E. G.;Tjaden, U. R.;van der Greef, J.. And the article was included in Journal of Chromatography in 1993.Category: thiazole This article mentions the following:

Various mass spectrometric techniques were explored for their ability to detect and identify minor components in benzothiazole-derived compounds, namely gas chromatog.-mass spectrometry, liquid chromatog.-mass spectrometry using a moving-belt, a thermospray and a particle-beam interface and liquid chromatog.-tandem mass spectrometry in combination with a thermospray interface. The necessary changes in the liquid chromatog. solvent systems were accomplished by translation of gradient runs into a series of isocratic runs, and a UV photodiode-array detector was used to trace the peaks. The methodol. developed and the advantages and limitations of the different techniques employed are discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

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. 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.Category: thiazole

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

Cyclization products from amino-substituted Bunte salts was written by Caldwell, J. B.;Milligan, Brian;Swan, J. M.. And the article was included in Journal of the Chemical Society in 1963.Electric Literature of C13H10N2S This article mentions the following:

PhNCS (I) (14 g.) 8.0 g. H₂NCH₂CH₂SSO₃H (Ia), and 100 ml. 50% aqueous C₅H₅N stirred vigorously 1.5 hrs., the pH maintained at 9 by the addition of 10% NaOH, the whole evaporated in vacuo, and the residue extracted with boiling EtOH gave 9.0 g. PhNHCSNHCH₂CH₂SSO₃Na (II), m. 177° (decomposition). To 2.75 g. II in 25 ml. H₂O at 0° was added 25 ml. 10N HCl, the whole swept 1 hr. with N, and the pH adjusted to 7 to give 3-anilino-5,6-dihydro-1,2,4-dithiazine (III); picrate m. 195-9° (decomposition). Similarly, I and o-H₂NC₆H₄SSO₃H (IV) gave 76% IVa (R = H, R¹ = PhNH), m. 160° (C₆H₆); I and 2,5-H₂N(Me₂N)C₆H₃SSO₃H (V) gave 51% IVa (R = Me₂N, R¹ = PhNH), m. 173°; MeNCS (VI) and IV gave 56% IVa (R = H, R¹ = MeNH), m. 139-40° (CCl₄); VI and V gave 65% IVa (R = Me₂N, R¹ = MeNH), m. 148-50° (petr. ether). IV (1 g.), 5 ml. CS₂, and 20 ml. 1:1 C₅H₅N-5% aqueous Na₂CO₃ refluxed 0.5 hr. gave 80% IVa (R = H, R¹ = SH), m. 181°; V and CS₂ gave IVa (R = Me₂N, R¹ = SH), m. 234°; and Ia and CS₂ gave 2-thiazoline-2-thiol, m. 105-6°. 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. 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.Electric Literature of C13H10N2S

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

Growth competition between Microcystis aeruginosa and Quadrigula chodatii under controlled conditions was written by Zhang, Ping;Zhai, Chunmei;Wang, Xiaoxian;Liu, Changhong;Jiang, Jihong;Xue, Yarong. And the article was included in Journal of Applied Phycology in 2013.Synthetic Route of C13H10N2S This article mentions the following:

Cyanobacteria are the dominant bloom-forming species in Lake Taihu. Understanding the competition among algae is important to control strategies for bloom formation and outbreaks in freshwater ecosystems. In this study, we demonstrate that the cyanobacterium Microcystis aeruginosa PCC7820 and the green alga Quadrigula chodatii FACHB-1080 exhibit a strong competitive inhibitory relationship under co-culture conditions, with the latter strain inhibiting the former. Several factors influence the competitive relationship between the two species, including nutrition, temperature, and organic/inorganic compounds Q. chodatii strongly inhibited M. aeruginosa growth through the inhibition of nitrogen utilization during co-culture. Temperature was also an influential determinant of the competition capacity between the two species under eutrophic conditions: at lower temperatures (15 °C), M. aeruginosa grew better than Q. chodatii, but the difference was not significant (p > 0.05), whereas at higher temperatures (25 °C, 35 °C), Q. chodatii grew significantly better than M. aeruginosa (p < 0.05). Furthermore, the Q. chodatii filtrate strongly inhibited the growth of M. aeruginosa. An anal. of the crude extracts of the algae culture filtrates from uni- and co-cultures using gas chromatog. mass spectrometry (GC/MS) indicated that algal metabolites, such as di-Bu phthalate and beta-sitosterol, might play a key role in the competition between algae. 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. 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.Synthetic Route of C13H10N2S

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