Tritylamine as an ammonia synthetic equivalent: preparation of primary amides

Abstract

A new synthetic route to primary amides via N-tritylamides was developed. The initially formed N-tritylamides, derived from acylation of tritylamine by activated carboxylic acid derivatives, were deprotected with trifluoroacetic acid at room temperature to the desired primary amides in good yields.

Identification of Cinnamic Acid Derivatives As Novel Antagonists of the Prokaryotic Proton-Gated Ion Channel GLIC

“…Concerning synthetic ligands of caffeic series ( x - Caf - y ; Figure a), standard procedures of esterification and amidation of caffeic acid ( Caf - CO 2 H ) afforded in relatively good yields the methyl and ethyl caffeates ( Caf - CO 2 Me and Caf - CO 2 Et ) and the amide derivative Caf - CONHEt , respectively. The primary amide Caf - CONH 2 was prepared according to a two-step procedure using tritylamine as a synthetic equivalent of ammonia . Finally, the dihydrocaffeic acid ( α , β - diH - Caf - CO 2 H ) was obtained by catalytic hydrogenation of caffeic acid.…”

“…The primary amide Caf-CONH 2 was prepared according to a two-step procedure using tritylamine as a synthetic equivalent of ammonia. 23 Finally, the dihydrocaffeic acid (α,β-diH-Caf-CO 2 H) was obtained by catalytic hydrogenation of caffeic acid. Reduction of methyl caffeate Caf-CO 2 Me by in situ prepared AlH 3 24 led to alcohol derivative Caf-CH 2 OH in modest yield.…”

Synthesis and Antibacterial Activity of N,N-Diethylamide Bearing Benzenesulfonamide Derivatives

“…It is important to note that amide formation is a fundamental reaction of great interest in organic chemistry [25,26]. The development of efficient methods for the synthesis of amides remains good tools because of their importance in chemistry and biology, with a wide range of industrial and pharmaceutical applications and as valuable intermediates in organic synthesis [27].…”

Production of Nitrogen‐Containing Compounds via the Conversion of Natural Microalgae from Water Blooms Catalyzed by ZrO2

“…Furthermore, nitrile is also platform molecules for medicine and polymer synthesis [20] . The current methods for preparing amides mainly include: 1) partial dehydration of ammonium carboxylate, [21] 2) aminolysis of acid chlorides, [22] acid anhydrides, [23] and esters, [24] 3) direct amidation of carboxylic acids, [25] 4) Beckman rearrangement of oximes, [26] 5) hydrolysis of nitrile [27] . There are also many synthetic methods of nitrile: 1) addition of HCN, [28] 2) cyanation of halogenated hydrocarbon, [29] 3) ammoxidation, [30] 4) dehydration of amides [31] .…”