A multi-component synthesis of N-substituted 2-amino-3-cyano pyrroles via ring-opening of nitroepoxides

Abstract

A multi-component synthesis of N-substituted 2-amino-3-cyano pyrroles from nitroepoxides, amines and malononitrile has been demonstrated.

Recent Advances on Pyrrole Synthesis through Different Annulation Modes

“…Scheme 87 Cyclization of primary amine, α-nitroepoxide and dialkyl acetylenedicarboxylate Based on similar strategy, the same team [125] demonstrated a multi-component reaction of α-nitroepoxides, amines and malononitrile to produce 2-amino-3-cyanopyrroles in the presence of K 2 CO 3 (Scheme 88).…”

A Copper‐Catalyzed Three‐Component Reaction for the Preparation of Polysubstituted Pyrroles from Alkynyl Ketones, Amines and Isocyanoacetates

“…Among this group of compounds, polysubstituted pyrroles have attracted tremendous attention for their potential physiological activities . Certain famous molecules in the polysubstituted pyrrole family, for example, Apricoxib, Aloracetam, Porphobilinogen, and Elopiprazole, occupy a prominent place in medicinal chemistry (Figure ). Therefore, the development of efficient protocols for the construction of these molecular architectures from readily available starting material is of great significance.…”

Catalyst-Free One-Pot Three-Component Synthesis of 2-Iminothiazoles from Nitroepoxides

“…23,25 In addition, bis-nucleophiles such as N-alkyl(thio)ethanolamine, 26 amidines, 27 diamines, 28 S-alkyl dithiocarbamates 23 and etc. [29][30][31] have been utilized in the reaction with nitroepoxides for the synthesis of valuable heterocyclic compounds including imidazoles, 1,3-thiazoles, benzodiazepines, thiazoline-2-thiones, and pyrazines.…”