Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/163328
Title: Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
Authors: Xia, Mengxin
Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
Keywords: Engineering::Chemical engineering
Issue Date: 2022
Source: Xia, M., Lambu, M. R. & Judeh, Z. M. A. (2022). Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles. Journal of Organic Chemistry, 87(18), 12115-12131. https://dx.doi.org/10.1021/acs.joc.2c01270
Project: NTU-SUG 
Journal: Journal of Organic Chemistry
Abstract: A one-pot, three-component cascade reaction between unprotected sugars, primary amines, and 3-oxoacetonitriles gave N-substituted 2,3,5-functionalized pyrroles or N-substituted 2,3,4-functionalized pyrroles in excellent yields and selectivities. The selectivity of the reaction was achieved by simple control of the sequence of substrate addition. The reaction showed a wide substrate scope, and various types of sugars, primary amines, and oxoacetonitriles reacted smoothly. The work demonstrates a highly desired simple reaction for embedding nitrogen into sugars to produce valuable N-heterocyclic compounds that are amenable to further modifications to natural products and drug intermediates.
URI: https://hdl.handle.net/10356/163328
ISSN: 0022-3263
DOI: 10.1021/acs.joc.2c01270
Rights: © 2022 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SCBE Journal Articles

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