701975-56-6

Upstream product

• 67-56-1 methanol 
• 2446-51-7 N-methoxybenzamide 
• 579-75-9 2-Methoxybenzoic acid 
• 593-56-6 N-methoxylamine hydrochloride 
• 21615-34-9 2-Methoxybenzoyl chloride 

Downstream Products

• 1360651-34-8 8-methoxy-3,4-diphenylisoquinolin-1(2H)-one 
• 126262-07-5 Y-05460M-A 
• 77674-99-8 6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate 
• 1440754-47-1 tert-butyl (3-methoxy-2-(methoxycarbamoyl)phenyl)carbamate 
• 1380546-67-7 2-(3-butylhept-2-enyl)-N,6-dimethoxybenzamide 
• 701975-75-9 2-propenyl (Z)-N,2-dimethoxybenzimidate 
• 701975-71-5 (Z)-N,2-dimethoxybenzenecarboximidoyl bromide 

Relevant academic research and scientific papers

Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones

Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.

Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst

Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.

Selective mono-alkylation of N-methoxybenzamides

We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.

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.).

Mild rhodium(III)-catalyzed C-H allylation with 4-vinyl-1,3-dioxolan-2-ones: Direct and stereoselective synthesis of (E)-allylic alcohols

A rhodium(III)-catalyzed C-H direct allylation reaction with 4-vinyl-1,3-dioxolan-2-ones has been developed. The reaction provides a facile and stereoselective access to substituted-(E)-allylic alcohols under mild and redox-neutral reaction conditions. Olefinic C-H activation is applicable, giving multifunctionalized skipped dienes in good yields. Minimal double-bond migration was observed.

Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction

A novel Pd-catalysed C-H activation reaction for the synthesis of biaryl imino/keto carboxylic acids is developed. This reaction underwent aryl amide directed C-H activation ortho-acylation followed by ring closing and ring opening processes to give a range of biaryl imino/keto carboxylic acids. Our methodology features the utilization of a cheap and green oxidant (TBHP) as well as readily available aldehydes.

Ruthenium-catalyzed isoquinolone synthesis through C-H activation using an oxidizing directing group

The oxidant directs: A mild, practical, efficient, and regioselective Ru-catalyzed isoquinolone synthesis with a broad substrate scope was reported (see scheme). In this redox neutral process, the aromatic CiH bond functionalization can be performed at room temperature without using any external oxidant. The mechanism of the reaction was probed, and it was found that CiH activation is the turnover-limiting step.

New heteroannulation reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H activation

A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Subs

Palladium-catalyzed alkoxylation of N-methoxybenzamides via direct sp 2 C-H bond activation

(Chemical Equation Presented) The palladium-catalyzed ortho-alkoxylation of N-methoxybenzamides has been demonstrated. With the CON-HOMe group as a directing group, the aromatic C-H bond can be functionalized efficiently to generate orthoalkoxylated derivatives in moderate to good yields.

Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone

The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone.