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

Mengxin Xia, Ziad Moussa, Zaher M.A. Judeh

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Article numbere202200367
JournalAsian Journal of Organic Chemistry
Volume11
Issue number9
DOIs
Publication statusPublished - Sept 2022

Keywords

  • carbohydrates
  • cascade reactions
  • pyrroles
  • three-component reactions

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Acetic Acid-Catalyzed Selective Synthesis of N-Substituted 2-Amino-3-Cyanopyrroles via a Three-Component Reaction Between Carbohydrates, Primary Amines and Malononitrile'. Together they form a unique fingerprint.

Cite this