18550-49-7

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 475089-07-7 4-bromo-2-(methylthio)aniline 
• 2258-42-6 formyl acetic anhydride 
• 29690-21-9 4-chloro-2-methylthiobenzenamine 
• 2987-53-3 2-(Methylthio)aniline 
• 137-07-5 2-amino-benzenethiol 
• 108429-46-5 (2-azidophenyl)(methyl)sulfane 
• 108429-49-8 1-(o-methylthiophenyl)-4,5-dihydro-5-hydroxy-1H-1,2,3-triazole 

Downstream Products

• 13372-62-8 N-methyl-o-aminophenyl methyl sulphide 
• 175694-99-2 (2-isocyanophenyl)(methyl)sulfane 
• 720675-16-1 bbenzo[d]thiazol-2-yldiphenylphosphine oxide 
• 883-93-2 2-Phenylbenzothiazole 
• 16112-21-3 2-(4-methylphenyl)-1,3-benzothiazole 
• 6265-92-5 2-(4-methoxy-phenyl)-benzothiazole 
• 1629-26-1 2-(4-fluorophenyl)-benzothiazole 
• 1211-32-1 2-(m-tolyl)benzo[d]thiazole 
• 40115-03-5 2-cyclohexyl-benzothiazole 
• 17626-86-7 2-isopropyl-benzothiazole 
• 120-75-2 2-Methylbenzothiazole 
• 33787-78-9 2-(1,4-dioxan-2-yl)benzo[d]thiazole 
• 6278-86-0 N₂-(4-bromophenyl)-1,3-benzothiazol-2-amine 
• 1843-21-6 N-phenyl-2-benzothiazolamine 

Relevant academic research and scientific papers

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.

Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles

We reveal here a visible-light promoted phosphorylation of 2-isocyanoaryl thioethers for the first time with concomitant C(sp3)-S bond cleavage and imidoyl C–S formation. Additionally, this method features the use of 3 mol% organic dye Rose Bengal as the photocatalyst without external transition-metal or peroxide oxidants, and provides a novel and environmentally friendly approach for the preparation of a variety of 2-phosphoryl benzothiazoles in moderate to good yields.

Cascade C(sp3)-S Bond Cleavage and Imidoyl C-S Formation: Radical Cyclization of 2-Isocyanoaryl Thioethers toward 2-Substituted Benzothiazoles

A cascade radical cyclization of 2-isocyanoaryl thioethers with H-phosphorus oxides, organoboronic acids, or alkyl radical precursors has been efficiently developed, providing a novel and highly efficient methodology to structurally diverse C2-substituted benzothiazole derivatives with broad functional group tolerance and good yields. This cascade radical process achieves the first cycloaddition of an imidoyl radical from isocyanide to sulfur atom, rending C(sp2)-S bond formation.

Developing potential agents against atherosclerosis: Design, synthesis and pharmacological evaluation of novel dual inhibitors of oxidative stress and Squalene Synthase activity

For the treatment of multifactorial and complex diseases, it has become increasingly apparent that compounds acting at multiple targets often deliver superior efficacy compared to compounds with high specificity for only a single target. Based on previous studies demonstrating the important antioxidant and anti-hyperlipidemic effect of morpholine and 1,4-benzo(x/thi)azine derivatives (A-E), we hereby present the design, synthesis and pharmacological evaluation of novel dual-acting molecules as a therapeutic approach for atherosclerosis. Analogues 1–10 were rationally designed through structural modifications of their parent compounds (A-E) in order for structure-activity relationship studies to be carried out. Most compounds showed a significant inhibition against Squalene Synthase activity exhibiting at the same time a very potent multimodal antioxidant (against lipid peroxidation and as free-radical scavengers) effect, thus bringing to light the 2-aryl-1,4-benzo(x/thia)zin-2-ol scaffold as an outstanding pharmacophore for the design of potent antioxidants. Finally, the replacement of the octahydro-1,4-benzoxazine moiety of lead compound D with its respective 1,4-benzothiazine (compound 4), although conserved (anti-hypercholesterolemic) or even improved (anti-hyperlipidemic) activity, did not preserve the anti-diabetic effect of D.

DECOMPOSITION OF ARYLAZIDES BY THF/n-BUTYLLITHIUM-II- -ISOLATION OF 1-ARYL-4,5-DIHYDRO-5-HYDROXY-1H-1,2,3-TRIAZOLES

By reaction of arylazides having no electron-withdrawing groups with the enolate ion of the acetaldehyde (formed by cycloreversion of THF in the presence of n-buthyllithium), 1-aryl-4,5-dihydro-5-hydroxy-1H-1,2,3-triazoles could be isolated and then characterized.Further reaction of such hydroxytriazolines with the same enolate ion afforded substantial amounts of the corresponding N-formylanilines , confirming their intermediacy in the previously reported decomposition of arylazides by THF/n-butyllithium.On the other hand, using alkoxides as bases, the preferred scheme of conversion of the hydroxytriazolines was found to be the known dehydration to 1-aryl-1H-1,2,3-triazoles.