22426-89-7

Upstream product

• 100-39-0 benzyl bromide 
• 57139-22-7 potassium p-methoxylbenzohydroxamate 
• 622-33-3 N-benzyloxyamine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 121-98-2 methyl 4-methoxybenzoate 
• 155164-68-4 4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one 

Downstream Products

• 63539-58-2 O-Benzoylsulfonyl-N-benzyloxy-p-anisimidsaeure 
• 6316-54-7 4-methoxy-benzoic acid benzyl ester 
• 874-90-8 4-methoxybenzonitrile 
• 281668-93-7 N-(4-bromobenzyl)-4-methoxy-benzamide 
• 281668-91-5 N-benzyloxy-N-(4-bromobenzyl)-4-methoxy-benzamide 
• 137042-73-0 C₁₅H₁₄BrNO₂ 

Relevant academic research and scientific papers

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

A metal-free iodine-mediated conversion of hydroxamates to esters

A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).

Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes

An efficient and transition-metal-free N-arylation of amides via the insertion of arynes into the N-H bonds in the N-alkoxy amides is described. A variety of the reactive functional groups including the reactive aldehyde carbonyl group, furan ring, carbon-carbon double bonds, and free N-H bond of indole are found to be compatible with this process. In particular, the protocol is applicable in the synthesis of structurally diverse N-aryl hydroxamates and hydroxamic acids derived from N-protecting amino acids and peptides. In the presence of multiple amide N-H bonds, the N-arylation reaction can proceed selectively in the N-H bonds of terminal N-OBn amides giving rise to the desired N-aryl hydroxamates.

N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole as a versatile reagent for synthesis O-alkylhydroxamic acids

(Chemical Equation Presented) Highly efficient reagent, N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole was synthesized and its applicability was demonstrated for the synthesis of O-alkyl hydroxamic acids. The efficiency of the reagent was evaluate

Design, synthesis and utilization of a novel coupling reagent for the preparation of O-alkyl hydroxamic acids

An efficient novel reagent, phosphoric acid diethyl ester 2-phenyl-benzimidazol-1-yl ester, was designed, and synthesized and its applicability was demonstrated for the preparation of O-alkyl hydroxamic acids. The O-alkyl hydroxamic acids of N-protected a

One-step synthesis of O-benzyl hydroxamates from unactivated aliphatic and aromatic esters

We have developed a simple and high yielding one-step method for the synthesis of hydroxamate derivatives directly from a broad range of unactivated esters and the anion of O-benzyl-hydroxylamine generated in situ. The reaction takes place in minutes at -

Convenient preparation of O-alkylhydroxamic acids using 2-acylpyridazin-3(2H)-ones

Treatment of O-alkylhydroxylamine hydrochlorides with 2-acyl-4,5- dichloropyridazin-3(2H)-ones in the presence of triethylamine or Amberlite IRA-67 in acetonitrile gave corresponding O-alkylhydroxamic acid derivatives in excellent yields. This is an effic

Reductive cleavage of N-O bonds using samarium(II) iodide in a traceless release strategy for solid-phase synthesis

(Metrix Presented) (i) p-anisoyl chloride, diisopropylethylamine, dichloromethane, 25 °C, 16 h. (ii) DBU, 4-bromobenzyl bromide, toluene, 25 °C, 48 h. (iii) SmI2/THF, 25 °C, 3 h. A strategy for making amides and ureas using a polymer-supported

A new synthesis of nitriles from N-alkoxyimidoyl halides with zinc

Both aliphatic and aromatic nitriles are obtained from the corresponding N-methoxy-, N-benzyloxy- or N-tert-butoxyimidoyl halides with zinc in a acetic acid/dimethylformamide mixture (1:1).