16715-75-6

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 104-84-7 para-methylbenzylamine 
• 1139705-26-2 4-methylphenyl imidazolesulfonate 
• 17200-29-2 5-chloro-benzoxazole 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 695-96-5 2-bromo-4-chlorophenol 
• 6326-27-8 p-methylbenzamidine hydrochloride 
• 83392-35-2 methyl 3-(4-methylphenyl)-3-oxopropanedithioate 
• 624-31-7 4-tolyl iodide 
• 95-55-6 2-amino-phenol 

Downstream Products

• 59098-30-5 5-chloro-2-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-benzooxazole 
• 65204-19-5 5-chloro-2-{4-[4-(4-chloro-5-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-benzooxazole 
• 65204-04-8 5-chloro-2-{4-[4-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-benzooxazole 
• 65204-30-0 5-chloro-2-{4-[4-(4,5-diphenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-benzooxazole 
• 53349-54-5 5-chloro-2-{4-[trans-2-(2-phenyl-benzofuran-6-yl)-vinyl]-phenyl}-benzooxazole 
• 37421-71-9 2-{4-[4-(5-chloro-benzooxazol-2-yl)-trans-styryl]-phenyl}-7-phenyl-2,7-dihydro-benzo[1,2-d;3,4-d']bis[1,2,3]triazole 
• 53415-39-7 5-chloro-2-[4-(4-trans-styryl-trans-styryl)-phenyl]-benzooxazole 
• 59136-16-2 5-chloro-2-{4-[2-(2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-benzooxazole 
• 65204-13-9 5-chloro-2-{4-[4-(4-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-benzooxazole 
• 59099-05-7 5-chloro-2-{4-[4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-benzooxazole 

Relevant academic research and scientific papers

Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles

Iron(III) chloride mediated para-selective C?H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole b

Stable Pd(0) Complexes with Ferrocene Bisphosphanes Bearing Phosphatrioxaadamantyl Substituents Efficiently Catalyze Selective C-H Arylation of Benzoxazoles by Aryl Chlorides

Versatile applications and unique performance of 1,1’-bis(diphenylphosphanyl)ferrocene (dppf) in coordination chemistry and catalysis prompted the search for its analogs. This contribution describes the synthesis of the first donor-unsymmetric dppf congeners bearing bulky and rigid 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantyl (CgP) donor groups, viz. Ph2PfcPCg (1) and Ph2PfcCH2PCg (2; fc=ferrocene-1,1’-diyl). Bis-phosphanes 1 and 2 were converted into air-stable Pd(0) complexes, [Pd(ma)(L^L)] (L^L=1 and 2; ma=maleic anhydride). Together with [Pd(ma)(dppf)], these complexes were applied as catalysts in Pd-catalyzed C?H arylation of benzoxazoles with aryl chlorides in n-butanol as an environmentally benign solvent. Among all catalysts tested in this study, complex [Pd(ma)(2)] performed the best, providing a high-yield and selective synthesis of 2-arylbenzoxazoles from a range of the generally less reactive chloroarenes at low catalyst loading (typically 1 mol.%). Under similar conditions, the structurally related heterocycles (e. g., 1-methylbenzimidazole and benzothiazole) did not react.

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.

Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst

Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

Pyrazole-3-carboxylates assisted N-heterocyclic carbene palladium complexes: synthesis, characterization, and catalytic activities towards arylation of azoles with arylsulfonyl hydrazides

Four mononuclear and dinuclear pyrazole-3-carboxylates assisted NHC–Pd complexes have been synthesized and characterized. Notably, the bridge-cleavage reactions of [Pd(μ-Cl)(Cl)(NHC)]2 with 1H-pyrazole-3-carboxylic acid afforded dinuclear complexes [(NHC)Pd(μ-1H-pyrazolato-3-carboxylate)]2, in which the 1H-pyrazolato-3-carboxylate was employed as a N^N^O dianionic chelating and bridging ligand. To further explore the structural features and catalytic properties of the complexes, 1-methyl-1H-pyrazole-3-carboxylic acid was introduced into the coordination with [Pd(μ-Cl)(Cl)(NHC)]2 and the corresponding mononuclear complexes (NHC)PdCl(1-methyl-1H-pyrazole-3-carboxylate) were obtained. The catalytic properties of the complexes in desulfitative arylation of azoles with arylsulfonyl hydrazides were initially investigated.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.

Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles

A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

A new superacid hafnium-based metal-organic framework as a highly active heterogeneous catalyst for the synthesis of benzoxazoles under solvent-free conditions

A new crystalline porous superacid material was prepared by sulfation of a Hf-MOF constructed from a 6-connected Hf node and 1,3,5-benzenetricarboxylate. The new superacid MOF with the presence of sulfate groups coordinated to a Hf-oxo cluster as superacid sites was found to be an effective heterogeneous catalyst for solvent-free heterocyclization for benzoxazole synthesis.

p-Toluenesulfonic acid-catalyzed metal-free formal [4?+?1] heteroannulation via N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization: One-pot access to 2-aryl/hetaryl/alkyl benzazole derivatives

A concise and direct one-pot [4?+?1] synthetic strategy for the construction of 2-substituted benzazoles such as benzoxazoles and benzothiazoles has been disclosed in high yields (80–98%) by cascade coupling reaction of 2-amino(thio)phenols with β-oxodithioesters. The current approach enables N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization in one-pot under solventless condition leading to diverse benzazoles without use of any external metal. A wide range of 2-amino(thio)phenols and β-oxodithioesters are compatible toward this transformation with excellent functional group tolerance. Furthermore, we preempt the wider implications of this novel strategy by demonstrating its compatibility toward versatile diversification of DNA Topoisomerase-II inhibitors.