2,3-Pyrrolidinediones. I. Preparation and Structure

2,3-Pyrrolidinediones. Ii. Thermal Decomposition

“…In the first paper of this series (1) the preparation of a number of 1,5-diaryl-2,3-pyrrolidinediones (I) was described and the structural character of the hetero-ring was discussed. Mention was made of the observation that compounds with the structure I are thermally decomposed to give carbon dioxide (2,3) and a cinnamylideneaniline (III) (3).…”

“…While no extensive investigation of the thermal decomposition of 2,3-pyrrolidinediones other than I was undertaken, a few observations were made on 1 Rackham Predoctoral Fellow 1950-1951. 2 Abstracted from a portion of the Ph.D. dissertation of Lynn R. Peters, University of Michigan, 1952.…”

“…Thus it would appear that substitution of the 4position with an aromatic ring not only stabilizes the 2,3-pyrrolidinedione toward decomposition, but also alters the course of the decomposition. Eight 1,5-diaryl-2,3-pyrrolidinediones (la through Ih) were prepared for the present study (1). All eight melt with gas evolution, and o-dichlorobenzene solutions of each evolve carbon dioxide upon being heated.…”

Pyrrolidine‐2,3‐diones: Synthesis, reactions and biological activity

“…The action of aniline and its derivatives with benzaldehyde and pyruvic acid, (MeCO.COOH) ( 39 ), has been studied in the early 1900s 35,36 . The course of the reaction is dependent on external conditions such as medium and temperature, upon the nature of the combination of the components [(PhN = CHPh + MeCO.COOH)], or [(PhNH 2 + PhCH = CHCO.COOH)], and upon the substituents in the benzene nucleus of aniline.…”

Synthesis of New Pyrrolo Heterocycles (I): Novel Synthesis of Pyrano[2,3‐c]pyrrole, Isoindoline, Pyrrolo[3,4‐b]pyridine, and Pyrrolo[3,4‐d]pyrimidine Derivatives

“…A part of our laboratory studies has focused on exploring the synthetic potentialities of 2,3‐dioxopyrrolidine derivatives as key intermediates of the synthesis of fused heterocycles with a pyrrolo nucleus. A variety of 1,5‐diaryl‐2,3‐dioxopyrrolidines could be readily obtained by adding the aromatic amines to the arylidine derivatives of pyruvic acid .…”