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Upstream product

• 369-36-8 6-fluoro-3-nitroaniline 
• 122-01-0 4-chloro-benzoyl chloride 
• 70886-33-8 5-nitro-benzooxazole 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 10403-47-1 2-bromo 5-nitroaniline 
• 83392-36-3 methyl 3-(4-chlorophenyl)-3-oxopropanedithioate 

Relevant academic research and scientific papers

A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst

The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcohols and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles.

Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives

The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.

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.

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.

A novel and efficient route for the synthesis of 5-nitrobenzo[d]oxazole derivatives

In this paper, we report a novel and efficient route for the synthesis of 5-nitrobenzoxazole derivatives starting from 2-fluoro-5-nitroaniline and various benzoyl chloride derivatives under solvent-free conditions at 130 °C in the presence potassium carbonate. Benzoyl chlorides easily underwent nucleophilic acyl substitution followed by intramolecular cyclization via concomitant removal of fluorine to obtain the title compounds in high yields.

Mechanistic study of oxidative aromatization using activated carbon-molecular oxygen system in the synthesis of 2-arylbenzazoles:focus on the role of activated carbon

Nineteen activated carbons, including sixteen tailor-made and three commercially available ones, were employed to investigate their role in the one-pot synthesis of 2-arylbenzazoles starting from 2-aminophenol, 1,2-diaminobenzene, or 2-aminobenzenethiol, and aldehyde via oxidative cyclization of intermediate phenolic Schiff base promoted by the activated carbon-molecular oxygen system. Tailor-made activated carbons were prepared from wood, coconut shell, and coal by the steam activation method or the chemical activation method. All activated carbons were characterized to clarify their properties, such as metal contaminants, specific surface area, porosity, and surface functionality. After examining their effects on reactivity in the oxidative aromatization, we found that the essential role of activated carbon in this oxidation system is concerned not with metal contaminants, specific surface area, pore volume, mean pore diameter, and surface oxygen groups evolving as CO2 at 900 °C but with surface oxygen groups evolving as CO during heating at 900 °C, such as carbonyl groups on the surface of activated carbon. Additionally, in the synthesis of 2-arylbenzoxazole, it was found that activated carbon would also promote the cyclization of the intermediate Schiff base.

Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-Methoxy-TEMPO

(Chemical Equation Presented) Setting the TEMPO: The scheme shows the efficient aerobic synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles where 4-methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy free radical (4-Methoxy-TEMPO) is used as the catalyst.

Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which:G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; andZ is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.