116016-01-4

Upstream product

• 865-50-9 iodomethane-d3 
• 623-08-5 N-methyl-p-toluidine 
• 1664-98-8 paraformaldehyde-d2 

Downstream Products

• 116016-03-6 C₂₁H₂₅⁽²⁾H₂N₃O₄ 
• 116016-02-5 C₂₁H₂₄⁽²⁾H₃N₃O₄ 
• 922543-66-6 4-methyl-N-(trideuteromethyl)aniline 
• 623-08-5 N-methyl-p-toluidine 
• 1306770-43-3 C₂₃H₂₀⁽²⁾H₂N₂ 
• 1306770-42-2 C₂₃H₁₉⁽²⁾H₃N₂ 

Relevant academic research and scientific papers

Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives

An unprecedented three-component domino oxidative coupling of diazocompounds for the efficient synthesis of α-azido-β-amino esters with non-activated dimethylamino compounds and simple TMSN3 was achieved. The main features of this method include metal-free catalysis, satisfactory functional group tolerance, general applicability in complex molecule architectures, and excellent diastereoselectivity in the presence of chiral auxiliaries. In addition, several related control experiments have been conducted to investigate the reaction mechanism.

Mechanism of oxidative amine dealkylation of substituted N,N-dimethylanilines by cytochrome P-450: Application of isotope effect profiles

Isotope effect profiles were determined for the deprotonation of a series of para-substituted N-methyl-N-(trideuteriomethyl)aniline cation radicals by pyridine and for hydrogen atom abstraction from the corresponding neutral amines by the tert-butoxyl radical. The profiles model reaction steps in two mechanisms commonly proposed for the oxidative dealkylation of amines by cytochrome P-450. Isotope effect profiles were also determined for the P-450 oxidation of the same set of N,N-bis(dideuteriomethyl)anilines by purified CYP2B1, expressed CYP2B1, phenobarbital-induced microsomal P-450, expressed CYP4B1, expressed CYP1A2, and purified CYP102 (BM3). The profiles for all of the P-450 oxidations were found to be experimentally indistinguishable from the hydrogen atom abstraction profile, and distinctly different from the deprotonation profile. This agreement provides strong evidence that the P-450 oxidatively dealkylates the amines by a hydrogen atom abstraction mechanism. Furthermore, the P-450 isotope effect profiles indicate that the reaction mechanism is conserved in both mammalian and bacterial enzymes.

Ruthenium-catalyzed alkylation of indoles with tertiary amines by oxidation of a sp3 CH bond and lewis acid catalysis

Ruthenium porphyrins (particularly [Ru(2,6-Cl2tpp)CO]; tpp = tetraphenylporphinato) and RuCl3 can act as oxidation and/or Lewis acid catalysts for direct C-3 alkylation of indoles, giving the desired products in high yields (up to 82

N-Demethylation of N,N-Dimethylanilines by the benzotriazole N-Oxyl radical: Evidence for a two-step electron transfer-proton transfer mechanism

"Chemical Equation Presented" The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, CF 3, CO2CH2CH3, CH3, OC6H5, OCH3) has been investigated in CH 3CN. Product analysis shows that the radical, 4-X-C6H 4N(CH3)CH2·, is first formed, which can lead to the N-demethylated product or the product of coupling with BTNO. Reaction rates were found to increase significantly by increasing the electron-donating power of the aryl substituents (p+ = -3.8). With electron-donating substituents (X = CH3, OC6H5, OCH3), no intermolecular deuterium kinetic isotope effect (DKIE) and a substantial intramolecular DKIE are observed. With electron-withdrawing substituents (X = CN, CF3, CO2CH2CH 3), substantial values of both intermolecular and intramolecular DKIEs are observed. These results can be interpreted on the basis of an electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism). By applying the Marcus equation to the kinetic data for X = CH3, OC 6H5, OCH3 (rate-determining ET), a reorganization energy for the ET reaction was determined (λ BTNO/DMA= 32.1 kcal mol- 1). From the self-exchange reorganization energy for the BTNO/BTNO- couple, a self-exchange reorganization energy value of 31.9 kcal mol-1 was calculated for the DMA·+/DMA couple.