Synthesis of new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones under catalyst-free and solvent-free conditions

Abstract

Several new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones were synthesized via the three-component condensation reaction of aldehydes, aromatic amines, and ethyl pyruvate under catalyst-free and solvent-free conditions. Also, 5-(4-hydroxyl-3-nitrophenyl)-1-(4-methoxy-phenyl)-3-(4-methoxyphenylamino)-1,5-dihydro-pyrrol-2-one was synthesized using oxime instead of aldehyde. The eco-friendly, simple procedure, green procedure, catalyst-free and solvent-free conditions, short reaction times, and high yields of the products are the advantages of this method.

A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

“…Based on this report, some authors later described several modifications of this synthetic procedure, and the uncatalyzed [25] or solvent-free [26] reaction, and the use of recyclable catalysts [27] were reported in the last few years. Interestingly, it was also established that such reaction can be performed under organocatalysis [28] and, taking the advantage of this fact, very recently, we achieved a highly enantioselective version of this reaction using 1,1′-bi-2-naphthol (BINOL)-derived chiral phosphoric acids as catalysts [29].…”

Brönsted-Acid-Catalyzed Asymmetric Three-Component Reaction of Amines, Aldehydes, and Pyruvate Derivatives. Enantioselective Synthesis of Highly Functionalized γ-Lactam Derivatives

“… This reaction consists of an initial Mannich reaction between aldimines 5 and enamines 6 , both generated by a concomitant condensation of amines 3 with aldehydes 1 and ethyl pyruvate 2a , respectively, followed by an intramolecular formation of an amide bond in adduct 7 due to the addition of the resulting amine to the carboxylic group (Scheme ). Some modifications of our synthetic procedure have been described later, such as the uncatalyzed or solvent-free reaction or the use of recyclable catalysts . It has been also established that such a reaction can be performed under organocatalysis .…”

Multicomponent Reactions in the Synthesis of γ-Lactams

“…Moreover, the uncatalyzed reaction under solvent-free conditions also affords efficiently 3-amino-1,5-dihydro-2H-pyrrol-2-ones 128 in moderate to very good yields (45-95%). 44…”