65718-88-9

Upstream product

• 111-14-8 oenanthic acid 
• 2528-61-2 Heptanoic acid chloride 
• 137-07-5 2-amino-benzenethiol 
• 638-45-9 1-Iodohexane 
• 116905-38-5 2-aminophenyl hexyl sulphide 
• 615-22-5 2-methylmercaptobenzothiazole 
• 111-25-1 1-bromo-hexane 
• 628-71-7 1-Heptyne 
• 615-43-0 2-iodophenylamine 
• 4368-51-8 tetraheptylammonium bromide 
• 32363-96-5 1,1-dibromohept-1-ene 
• 1141-88-4 2-Aminophenyl disulfide 
• 111-71-7 heptanal 
• 609-73-4 o-nitroiodobenzene 

Relevant academic research and scientific papers

Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes

Eosin Y-catalyzed one-pot coupling and cyclization of o-substituted anilines with aldehydes to form benzoxazoles and benzothiazoles under mild condition has been developed. The reaction scope was broadly tolerant of various 2-substituted anilines and aldehydes. The desired products were obtained in high yields with the use of eosin Y as a photocatalyst under a substantial refinement of reaction conditions in comparison with previous literature. Based on the experimental results observed, a plausible mechanism involving a radical process has been proposed.

Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide

The invention discloses a method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide. According to the method, a 1-phenyl-3-butyne-2-ketone compound andan o-aminothiophenol compound are taken as raw materials, potassium tert-butoxide is taken as a catalyst and tert-butyl alcohol is taken as a solvent to prepare the 1, 3-benzothiazole derivative at high efficiency and high yield. According to the method, no metal catalyst is used, the method is environmentally friendly, reaction conditions are mild, operation is easy, the 1, 3-benzothiazole derivative can be obtained only by conducting simple column chromatography separation on a product obtained after the reaction is finished, a new green and efficient way is developed for preparation of the1, 3-benzothiazole derivative, and certain application prospects are achieved.

An efficient synthesis of benzothiazole using tetrabromomethane as a halogen bond donor catalyst

An efficient and mild protocol has been developed for the synthesis of 2-substituted benzothiazole under solvent- and metal-free conditions using CBr4 as the catalyst. This process involves the activation of a thioamide through halogen bond formation between the sulphur atom of the thioamide and bromine atom of the CBr4 molecule. The presence of halogen-bonding interaction between N-methylthioamides and tetrabromomethane has been demonstrated with several control experiments, spectroscopic analysis and density functional theory (DFT). This methodology has a wide substrate scope for the synthesis of both 2-alkyl and 2-aryl substituted benzothiazoles.

Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

Ni-Catalyzed Reductive Liebeskind-Srogl Alkylation of Heterocycles

Herein we present a Ni-catalyzed alkylation of C-SMe with alkyl bromides for the decoration of heterocyclic frameworks. The protocol, reminiscent to the Liebeskind-Srogl coupling, makes use of simple C(sp2)-SMe to be engaged in a reductive coupling. The reaction is suitable for a preponderance of highly valuable heterocyclic motifs. In addition to cyclic bromides, noncyclic alkyl bromides are well accommodated with exquisite levels of retention over isomerization. The protocol is scalable and permits orthogonal couplings in the presence of other functionalization handles.

Controllable assembly of the benzothiazole framework using a CC triple bond as a one-carbon synthon

A concise and efficient protocol to assemble diverse benzothiazole derivatives in high yields was provided via copper catalyzed tandem cyclization with o-haloanilines, elemental sulfur and terminal alkynes as raw materials. In this protocol, C atoms on the CC triple bond were controllably involved in the construction of the benzothiazole framework and multiple carbon-heteroatom bonds through divergent routes.

A simple and efficient route for synthesis of 2-alkylbenzothiazoles

The condensation of 2-aminothiophenol with aliphatic aldehydes in the presence of 4? molecular sieves, followed by oxidation with silica gel supported pyridinium chlorochromate offers a simple and efficient route to 2-alkylbenzothiazoles.

Synthesis of Quinoline-Based NNN-Pincer Nickel(II) Complexes: A Robust and Improved Catalyst System for C-H Bond Alkylation of Azoles with Alkyl Halides

The quinoline-based pincer nickel(II) complexes κN,κN,κN-{R2N-C6H4-(μ-N)-C9H6N}NiX ((R2NNNQ)NiCl: R = Me, 2a; R = Et, 2b) were synthesized by the reaction of the ligand precursors (R2NNNQ)H (R = Me, 1a; R = Et, 1b) with (DME)NiCl2 in the presence of Et3N. Similarly, the pincer nickel(II) derivatives (R2NNNQ)NiX (R = Me, X = Br, 3a; R = Et, X = Br, 3b; R = Me, X = OAc, 4a) were obtained by treatment of the ligands (R2NNNQ)H with the nickel precursor (THF)2NiBr2 or Ni(OAc)2. All of these complexes were characterized by 1H and 13C NMR spectroscopy as well as by elemental analysis. Further, the molecular structures of 2a and 3a,b were elucidated by X-ray crystallography. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles with various unactivated alkyl halides containing β-hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway.

Quaternary ammonium salt as alkylation agent in three-component reactions for the synthesis of benzothiazoles in water

Substituted benzothiazoles are synthesized by metal-catalyst-free three-component reactions of o-iodoaniline, quaternary ammonium salt, and sulfur powder in water with moderate-to-excellent yields up to 95%. This journal is the Partner Organisations 2014.

Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed tandem reaction of β,β-Dihalidestyrenes with 2,2′- Disulfanediyldianilines

A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)2-catalyzed tandem reaction of β,β-dihalidestyrenes with 2,2′-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)2. Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield. Georg Thieme Verlag Stuttgart, New York.