Abstract
A convenient and easy method is described for the formation of carboxamides from carboxylic acids and primary amines in solventless conditions using infrared (IR) light. Thus, under IR light, cinnamic acid derivatives and amines can produce yields ranging from 50% to 85% of the resulting amide.
Highlights
Caffeic acid phenethyl ester (CAPE) is a natural phenolic chemical compound found in a variety of plants
While there are few reports of amide synthesis from cinnamic derivatives, there are some reports that amides derived from cinnamic acids have antioxidant, anti-atherogenic, antiviral, cytotoxic and antifungal properties, with sundry action mechanisms from enzyme inhibition to free radical scavenging. The synthesis of these compounds from different functional groups has recently been described by different authors, who have synthesized them from ketones; from aldehydes; from acid halides via Schotten-Baumann reaction [19]; from carboxylic acid; using amines and a molecular sieve [21]; from amines with nanosulfated titanium dioxide [22]; using epimerization-prone carboxylic acids and amines with T3P and Pyridine [23]; using triacyloxyboranes [24]; using trimethylaluminium [25]; with tosyl chloride in solventless conditions [26]; with urea using microwaves [27]; using solid phase synthesis with polymer bound reagents [28]; using isonitriles [29]; from esters and lactones [30]; from imines [31]; and from esters. On this occasion and as a part of the research agenda of the bioactive molecules program, we report the synthesis of amides from cinnamic acid analogs and from phenylacetic acid with aliphatic amines in the absence of solvent
Cinnamic acid analogs were prepared in good yields with short reaction times; this allows to an efficient preparation and purification
Summary
Caffeic acid phenethyl ester (CAPE) is a natural phenolic chemical compound found in a variety of plants. It is a component of propolis from honeybee hives, used as a sealant and to keep the hive clean from fungus and other contaminants [1]. Several in vitro pharmacokinetic effects have been reported for CAPE, including a positive effect on reducing. How to cite this paper: Martínez-Soriano, P.A., et al (2015) Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions.
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