Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones was written by Subramani, Muthuraman;Rajendran, Saravana Kumar. And the article was included in European Journal of Organic Chemistry in 2019.Related Products of 3326-13-4 This article mentions the following:
Amides are indispensable building blocks of biol. systems, pharmaceuticals, and materials. We report a highly selective method for the synthesis of amides via transamidation process. Transamidation of N-acyl-2-piperidones with a broad range of amines is demonstrated under exceedingly mild and metal-free reaction condition that relies on the amide bond twist to weaken the amidic resonance. Transamidation proceeds under the neat condition at room temperature, in short reaction times (30-90 min) with good yields. Considerable variation is tolerated with both amine and imide substrates. Of note, amines bearing carboxylic acids (glycine and serine) and hydroxyl groups (dopamine, tyramine, etc.) are well tolerated which are otherwise problematic under the metal-catalyzed protocol. The current method is applicable for transamidation of both alkyl and aryl-N-acyl-2-piperidones. The practical value of the method is highlighted by the synthesis of four natural product amide alkaloids in high yields under mild reaction conditions. In the absence of nucleophilic amines, N-acyl-2-piperidones undergoes esterification with EtOH at elevated temperature Single crystal X-ray anal. of an N-acyl-2-piperidone shows amide bond twist, 蟿 = -20.39掳 and pyramidalization, 蠂N = -11.73掳. This weakens the amidic conjugation and might be the factor controlling the reactivity and selectivity of these imides. The N-acyl-2-piperidone scaffold could be useful in the synthesis of pharmaceuticals and materials. In the experiment, the researchers used many compounds, for example, 1-Acetylpiperidin-2-one (cas: 3326-13-4Related Products of 3326-13-4).
1-Acetylpiperidin-2-one (cas: 3326-13-4) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Related Products of 3326-13-4
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem