14072-67-4Relevant articles and documents
One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
Bobal, Pavel,Otevrel, Jan,Svestka, David
, p. 25029 - 25045 (2020/07/14)
We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
Method for synthesizing alpha-alkylarylacetamide
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Paragraph 0076; 0077; 0078; 0079; 0080, (2017/06/02)
The invention discloses a method for synthesizing alpha-alkylarylacetamide. In a reaction vessel, aromatic acetonitrile, compound alcohol, a transition metal catalyst metal rhodium complex, alkali, a phosphine ligand and an organic solvent are added; the reaction mixture is subjected to a reaction under a temperature of 130 DEG C in a microwave reactor or under magnetic stirring; the mixture is cooled to room temperature, and is processed through column separation, such that a target compound is obtained. According to the invention, nitrile and alcohol are adopted as initial raw materials; under the participation of the transition metal catalyst, the phosphine ligand and alkali, alpha-alkylarylacetamide is directly synthesized. The reaction has three significant advantages: (1) commercialized or easy-to-prepare nitrile and almost nontoxic alcohol are adopted as initial raw materials; and (2) the reaction has high atomic economy. Therefore, the reaction meets the requirements of green chemistry, and has a good development prospect.
Direct coupling of arylacetonitriles and primary alcohols to α-alkylated arylacetamides with complete atom economy catalyzed by a rhodium complex-triphenylphosphine- potassium hydroxide system
Li, Feng,Zou, Xiaoyuan,Wang, Nana
, p. 1405 - 1415 (2015/05/19)
A direct synthesis of α-alkylated arylacetamides from arylacetonitriles and primary alcohols has been accomplished for the first time. In the presence of the rhodium complex [Rh(cod)Cl]2/triphenylphosphine/potassium hydroxide system, the desired α-alkylated arylacetamides were obtained in 74-92% yield under microwave conditions. The experimental results in this paper are in sharp contrast with previous reports, where the coupling of arylacetonitriles and primary alcohols produced the α-alkylated arylacetonitriles. Mechanistic investigations show that arylacetonitriles are first α-alkylated with primary alcohols to produce α-alkylated arylacetonitriles, which are further hydrated with the water resulting from the α-alkylation step to produce α-alkylated arylacetamides. More importantly, this research shows the potential of developing completely atom-economical reactions that involve the hydrogen autotransfer (or hydrogen borrowing) process.
Selective hydrolysis of nitriles to amides using NaOH-PEG under microwave irradiation
Bendale, Pravin M.,Khadilkar, Bhushan M.
, p. 1713 - 1718 (2007/10/03)
We describe here an efficient, rapid and selective method for the conversion of nitriles in to their corresponding amides in the presence of PEG-400, aqueous sodium hydroxide system under microwave irradiation.
