1268451-51-9

Upstream product

• 1079-02-3 benzoic acid-2,3,4,5,6-d5 
• 4165-57-5 bromobenzene-d5 
• 43019-90-5 benzoyl chloride-d5 
• 593-56-6 N-methoxylamine hydrochloride 

Downstream Products

• 1268451-54-2 C₁₅H₉⁽²⁾H₄NO 
• 1456693-84-7 3-hydroxy-2-methoxy-3-phenylisoindolin-1-one 
• 1380546-62-2 2-(3-butylhept-2-enyl)-N-methoxybenzamide 
• 1380546-80-4 C₁₉H₂₅⁽²⁾H₄NO₂ 
• 1380546-90-6 2-(3-butylhept-2-enyl)-6-(1-cyclohexylidene-3-hydroxypropan-2-yl)-N-methoxybenzamide 
• 1380546-89-3 2-(3-butylhept-2-enyl)-N-methoxy-6-(1-methoxy-4-propylhept-3-en-2-yl)benzamide 
• 1380546-87-1 2-(3-butylhept-2(Z)-enyl)-N-methoxy-6-(3-phenylhept-2-enyl)benzamide 
• 1380546-83-7 2,6-bis(3-butylhept-2-enyl)-N-methoxybenzamide 

Relevant academic research and scientific papers

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.

Cp?CoIII-catalyzed formal [4+2] cycloaddition of benzamides to afford quinazolinone derivatives

A Cp?CoIII-catalyzed arene C-H bond amidation/annulation of benzamides was developed to afford quinazolinone derivatives in one-pot with high yields and broad substrate scope. This method could be applied to the synthesis of quinazolinone drugs and late-stage modification of natural products.

Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties

Rhodium-catalyzed C-H activation/annulation reactions of ketenimines with N-methoxybenzamides furnished 3-aminoisoindolin-1-ones and 3-(diarylmethylene)isoindolin-1-ones. The synthesized 3-(diarylmethylene)isoindolin-1-ones exhibited aggregation induced emissions in aqueous tetrahydrofuran solution and strong green-yellow emissions in solids.

Ruthenium-Catalyzed C-H Alkynylation of Aromatic Amides with Hypervalent Iodine-Alkyne Reagents

An efficient C-H activation method for the ortho alkynylation of aromatic N-methoxyamides with hypervalent iodine-alkyne reagent using a ruthenium catalyst is described. The reaction proceeds under mild reaction conditions with broad substrate scope. A possible catalytic cycle involving a ruthenium carboxylate assisted C-H bond cleavage is proposed from the preliminary mechanistic evidence.

Solvent-Controlled, Tunable β-OAc and β-H Elimination in Rh(III)-Catalyzed Allyl Acetate and Aryl Amide Coupling via C-H Activation

The Heck reaction between arenes and allyl acetate has led to cinnamyl derivatives and allyl products depending on the regioselectivity of β-elimination. The regioselectivity can be controlled by the solvent in the Rh(III)-catalyzed arene-allyl acetate coupling via C-H activation: (1) in THF, cinnamyl derivatives via β-H elimination were generated; (2) in MeOH, allyl products via β-OAc elimination were produced. Both routes have advantages such as excellent γ-selectivity toward allyl acetate, good to excellent yields, and broad substrate scope.

Rh-catalyzed oxidizing group-directed ortho C-H vinylation of arenes by vinylstannanes

An efficient method for the synthesis of functionalized vinyl arenes from the reaction of N-methoxybenzamides or N-phenoxyacetamides with vinylstannanes via rhodium(III)-catalyzed C-H activation is described. The application of the methodology for the synthesis of a natural product thalactamine and a 7-membered ring oxepine are also demonstrated.

Tunable arylative cyclization of 1,6-enynes triggered by rhodium(III)-catalyzed C-H activation

Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an N-Michael addition process or hydrobenzofurans through a C-Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of CpRhIII-catalyzed C-H activation cascade reactions.

Synthesis of phenanthridinones from N-methoxybenzamides and aryltriethoxysilanes through RhIII-catalyzed C-H and N-H bond activation

An efficient method for the one-pot synthesis of substituted phenanthridinone derivatives from N-methoxybenzamides and aryltriethoxysilanes through rhodium-catalyzed dual C-H bond activation and annulation reactions is described. A double-cycle mechanism is proposed to account for this catalytic reaction. In addition, isotope-labeling studies were performed to understand the intimate mechanism of the reaction. Keeping active: The rhodium-catalyzed C-H bond activation and annulation reactions of N-methoxybenzamides with aryltriethoxysilanes to give substituted phenanthridinone derivatives in good-to-excellent yields is described. Copyright

Rhodium(III)-catalyzed oxidative ciH coupling of N-methoxybenzamides with aryl boronic acids: One-pot synthesis of phenanthridinones

General solution: An efficient rhodium-catalyzed dual CiH bond activation and cyclization of N-methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CiC and CiN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3. Copyright

Rh(III)-catalyzed Directed C-H Olefination using an oxidizing directing group: Mild, efficient, and versatile

An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.