7438-09-7Relevant academic research and scientific papers
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.
Ruthenium-Catalyzed Synthesis of N-Methylated Amides using Methanol
Paul, Bhaskar,Panja, Dibyajyoti,Kundu, Sabuj
supporting information, p. 5843 - 5847 (2019/08/26)
An efficient synthesis of N-methylated amides using methanol in the presence of a ruthenium(II) catalyst is realized. Notably, applying this process, tandem C-methylation and N-methylation were achieved to synthesize α-methyl N-methylated amides. In addition, several kinetic studies and control experiments with the plausible intermediates were performed to understand this novel protocol. Furthermore, detailed computational studies were carried out to understand the mechanism of this transformation.
Lipase-catalyzed transformations using poly(ethylene glycol) as solvent
Kidwai, Mazaahir,Poddar, Roona,Bhardwaj, Saurav
experimental part, p. 113 - 118 (2011/12/15)
Candida antarctica lipase catalyzes a number of elementary reactions like alcoholysis, ammoniolysis and aminolysis in poly(ethylene glycol) (PEG) media. Reaction rates were comparable to or better than those observed in conventional organic reaction media and ionic liquids. It is envisaged that PEGs could have added benefits for performing biotransformations with highly polar substrates, which are sparingly soluble in common organic solvents.
Room-temperature debenzylation of N-benzylcarboxamides by N-bromosuccinimide
Kuang, Liping,Zhou, Jing,Chen, Sheng,Ding, Ke
, p. 3129 - 3134 (2008/03/28)
A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or disubstituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism. Georg Thieme Verlag Stuttgart.
