Reactivity of pyrrol-2-ones. (review)

Abstract

Published data on the chemical transformations of pyrrol-2-ones are reviewed and analyzed. The extensive synthetic possibilities of compounds containing a pyrrolone ring in the synthesis of various heterocyclic compounds with complex structures are demonstrated. The reactions are arranged according to the reaction centers of the pyrrol-2-ones: The methylene unit, the C=C double bond, the electron-deficient carbon atom of the carbonyl group.

Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids

“…Five-membered N -containing heterocycles are important chemical frameworks that represent the core structures of many natural products, pharmaceutically active compounds, or agrochemicals. − Some examples of biologically active compounds that contain differently substituted N -heterocycles with different degrees of unsaturation and levels of oxidation are shown in Figure . The fully saturated pyrrolidine, for instance, is the common structure of a number of hNK1 antagonists represented with structure 1 , and the aromatic pyrrole is contained in the naturally occurring pyrrolnitrin ( 2 ), which shows antimycobacterial and antifungal activities. − Pyrrolidin-2-ones and pyrrolin-2-ones are found in compounds such as (−)-Clausenamide ( 3 ), isolated from Clausena lansium , , and related derivatives, , which are multitarget nootropics, or in structures of type 4 , acting as mineralocorticoid receptor antagonists, respectively.…”