Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/163329
Title: Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile
Authors: Xia, Mengxin
Moussa, Ziad
Judeh, Zaher M. A.
Keywords: Engineering::Chemical engineering
Issue Date: 2022
Source: Xia, M., Moussa, Z. & Judeh, Z. M. A. (2022). Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile. Asian Journal of Organic Chemistry, 11(9), e202200367-. https://dx.doi.org/10.1002/ajoc.202200367
Project: NTU-SUG 
Journal: Asian Journal of Organic Chemistry
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.
URI: https://hdl.handle.net/10356/163329
ISSN: 2193-5807
DOI: 10.1002/ajoc.202200367
Rights: © 2022 Wiley-VCH GmbH. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SCBE Journal Articles

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