Gesellschaft Deutscher Chemiker
Keine Benachrichtigungen
Sie haben noch keine Lesezeichen
Abmelden

Artikel

Acetic Acid‐Catalyzed Selective Synthesis of N‐Substituted 2‐Amino‐3‐Cyanopyrroles via a Three‐Component Reaction Between Carbohydrates, Primary Amines and Malononitrile

Von Wiley-VCH zur Verfügung gestellt

A simple three-component synthesis of N-substituted 2-amino-3-cyanopyrrole key framework is developed from the reaction between unprotected carbohydrates, malononitrile and primary amines.


Abstract

Direct conversion of unprotected carbohydrates to N-heterocycles is challenging and highly desirable. A simple three-component synthesis of N-substituted 2-amino-3-cyanopyrrole key framework is developed from the reaction between unprotected carbohydrates, malononitrile, and primary amines. The reaction proceeded under mild reaction conditions (AcOH catalyst, EtOH, 60 °C, 2 hours), tolerated a wide substrate scope, worked smoothly on a 4 g scale, and gave the pyrroles in up to 86% yield. The pyrroles were also converted into functional intermediates to demonstrate their versatility. NMR and LC–MS experiments supported a proposed cascade reaction mechanism. The approach demonstrates a robust upcycling process for the challenging synthesis of highly functionalized N-heterocyclic compounds from unprotected carbohydrates.

Zum Volltext

Überprüfung Ihres Anmeldestatus ...

Wenn Sie ein registrierter Benutzer sind, zeigen wir in Kürze den vollständigen Artikel.