114331-87-2

Upstream product

• 86399-83-9 N-[2-((4-methoxybenzoyl)oxy)phenyl]-4-methoxybenzamide 
• 201230-82-2 carbon monoxide 
• 95-55-6 2-amino-phenol 
• 329939-01-7 N-(2-iodophenyl)-4-methoxybenzamide 
• 7464-45-1 2-nitrophenyl 4-methoxybenzoate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 132283-36-4 C₂₀⁽¹³⁾CH₁₇NO₄ 
• 838-34-6 2-(p-methoxyphenyl)benzoxazole 

Relevant academic research and scientific papers

Cationic N-Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines

The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.

Divergent reactivities of o-haloanilides with CuO nanoparticles in water: A green synthesis of benzoxazoles and o-hydroxyanilides

In the present study, three divergent reaction paths emerged when o-haloanilides were subjected to CuO nanoparticles in water. o-Halo (I, Br) phenylbenzamides in the presence of CuO nanoparticles and Cs2CO 3 in water at 100 °C provided o-hydroxyphenyl benzamides as the major product. However, a complete change in selectivity was observed in the presence of an organic base/ligand (TMEDA), giving 2-arylbenzoxazole as the exclusive product. The above selectivities were not clearly distinct when the corresponding alkylamides were treated either in the presence or absence of the ligand. A number of o-halophenyl alkylamides provided either exclusively o-dehalogenated products or a mixture of o-dehalogenated and o-hydroxylated products, but none gave 2-alkylbenzoxazoles. In addition to the above selectivities, the use of an environmentally friendly solvent (water) and base, and the recyclability of the catalyst make this procedure a benign alternative to the existing methods for the synthesis of these molecules, viz. o-hydroxybenzamides and o-arylbenzoxazoles.

N-(2-hydroxyaryl)benzamide synthesis from 2-nitroaryl benzoates via an Indium-mediated reduction-migration reaction

A one-pot reduction-triggered N-(2-hydroxyaryl)benzamide synthesis from 2-nitroaryl benzoate substrates was investigated. In the presence of indium/AcOH in THF/H2O, 2-nitroaryl benzoates produced reasonable yields of the benzo group migrated N-

Smart cleavage reactions: The synthesis of benzimidazoles and benzothiazoles from polymer-bound esters

The preparation of an array of benzimidazoles and benzothiazoles from polymer-bound esters is described. Polymer-bound esters were treated with 2-aminothiophenols or 1,2-phenylenediamines in the presence of a Lewis acid to afford the corresponding benzothiazole or benzimidazole cleavage products. The reaction of 2-aminophenols with the polymer-bound esters failed to give the desired benzoxazole products using this procedure.

Hypervalent iodine in synthesis 69: An efficient synthesis of 2-arylbenzoxazoles via the palladium-catalysed carbonylation and condensation of diaryliodonium salts and o-aminophenols

An efficient synthetic method is reported in which 2-arylbenzoxazoles have been prepared in good to excellent yields under mild reaction conditions by the palladium-catalysed carbonylation of diaryliodonium salts with o-aminophenols followed by dehydrative cyclisation.

Antithrombotic agents

This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

N2-aroylanthranilamide inhibitors of human factor Xa

Reversal of the A-ring amide link in 1,2-dibenzamidobenzene 1 (fXa K(ass) = 0.81 x 106 L/mol) led to a series of human factor Xa (hfXa) inhibitors based on N2-aroylanthranilamide 4. Expansion of the SAR around 4 showed that only smal

Synthesis and microbiological activity of some N-(o-hydroxyphenyl)benzamides and phenylacetamides as the possible metabolites of antimicrobial active benzoxazoles: Part II

The synthesis of some N-(o-hydroxyphenyl)benzamides and benzacetamides (2a-2p) in order to determine their in vitro antimicrobial activity against two Gram-positive bacteria, three Gram-negative bacteria and the fungus Candida albicans is described. The new compounds were compared with several control drugs. The derivative 2g, 4-amino-N-(o-hydroxyphenyl)benzamide, was found active at an MIC value of 25 μg/ml against the Gram-negative microorganism Klebsiella pneumoniae. Most of the compounds exhibited antibacterial activity at an MIC value of 25 μg/ml against Pseudomonas aureginosa. For the antifungal activity against C. albicans, compounds 2e, 2h and 2m were found more active than the other derivatives (MIC 12.5 μg/ml). The antimicrobial activity of some of these benzamide and phenylacetamide derivatives (2a, 2b, 2f, 2g, 2h and 2k), possible metabolites of benzoxazoles, was also compared with that of the cyclic analogues 3-8. Compound 2f possesses two dilutions better antifungal activity than its cyclic analogue the benzoxazole derivative 5 against C. albicans, while having one dilution better antibacterial activity against Streptococcus faecalis and K. pneumoniae. (C) 2000 Elsevier Science S.A.

The conversion of mixed N,O-diacylated 2-aminophenols to 2-substituted benzoxazoles

When N,O-diacylated 2-aminophenols that have different acyl substituents on nitrogen and oxygen are treated with p-toluenesulfonic acid in refluxing xylenes, mixtures of benzoxazoles are produced. The major product is the benzoxazole in which the substituent at the 2-position is derived from the acyl group on nitrogen. This product may arise from an unusual case of acid- mediated neighboring amido-group assisted hydrolysis.

Synthesis of 2-Arylbenzoxazoles via the Palladium-Catalyzed Carbonylation and Condensation of Aromatic Halides and o-Aminophenols

A new synthetic method is reported in which 2-arylbenzoxazoles can be prepared by palladium-catalyzed condensation of aryl halides with o-aminophenols followed by dehydrative cyclization.This method is tolerant of a wide variety of functional groups on either aromatic ring and gives good to excellent yields of products.An aliphatic vicinal amino alcohol gave a bis-acylated product as well as a chlorine-containing product with only a small amount of the desired 2-aryloxazole being formed.Methyl iodide and benzyl bromide gave only alkylated products.