114-33-0Relevant articles and documents
Metal-free reductive cleavage of N-O bonds in weinreb amides by an organic neutral super-electron donor
Cutulic, Sylvain P. Y.,Murphy, John A.,Farwaha, Hardeep,Zhou, Sheng-Ze,Chrystal, Ewan
, p. 2132 - 2136 (2008)
The scope of neutral organic super-electron donors as reducing agents has been extended to include the reductive cleavage of N-O bonds in Weinreb amides. This methodology proved to be applicable to a large array of substrates to afford their reduced counterparts in good to excellent yields. The variation in reactivity within the set of tested amides is rationalised. Georg Thieme Verlag Stuttgart.
Tandem Transformation of Aldoximes to N-Methylated Amides Using Methanol
Paul, Bhaskar,Maji, Milan,Panja, Dibyajyoti,Kundu, Sabuj
, p. 5357 - 5362 (2019)
Tandem conversion of aldoximes to N-methylated amides with methanol in presence of a single Ru(II) catalyst is accomplished through the Ru(II)-mediated rearrangement followed by the reductive N-methylation. Employing this protocol, several aldoximes were directly transformed to the N-methylated amides using methanol. Kinetic experiments with H218O advocated that the aldoxime is acted as the nucleophile during the aldoxime to amide rearrangement process. Involvement of nitrile intermediate during this transformation is realized from the kinetic study. (Figure presented.).
Preparation method of racemic nicotine
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Paragraph 0048-0056, (2021/10/30)
The invention discloses a preparation method of racemic nicotine. The method comprises the following steps of: preparing methyl nicotinamide from nicotinoyl chloride and methylamine under alkaline conditions; condensing the methyl nicotinamide with monochloroacetone to obtain N-methyl-N-(2-oxypropyl) nicotinamide; carrying out aldol condensation reaction on theN-methyl-N-(2-oxypropyl) nicotinamide to obtain 1-methyl-5-(pyridine-3-yl)-1, 2-dihydro-3H-pyrrole-3-ketone; and finally performing reduction to obtain the racemic nicotine. The invention provides a new route for synthesizing the racemic nicotine; the cheap and easily available nicotinoyl chloride and methylamine are adopted as starting raw materials, so that the cost of the raw materials is low; the whole reaction synthesis route is relatively short, the operation is simple, the reaction condition is mild, the post-treatment is simple; the yield of the synthesized racemic nicotine is high; and the method is suitable for industrial large-scale production.
Atom-Economical and Tandem Conversion of Nitriles to N-Methylated Amides Using Methanol and Water
Paul, Bhaskar,Maji, Milan,Kundu, Sabuj
, p. 10469 - 10476 (2019/11/05)
A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture. Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. Kinetic experiments using H2O18 and CD3OD suggested that water and methanol were the source of the oxygen atom and methyl group, respectively, in the final N-methylated amides. Importantly, the participation of active Co(I)-H species in this transformation was realized from the control experiment. The kinetic isotope effect (KIE) study suggested that the activation of the C-H bond of methanol was a kinetically important step. The Hammett plot confirmed that the reaction was faster with the electron deficient nitriles. In addition, the plausible pathway for the formation of N-methylated amides from the nitriles was supported by the computational study.
