Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles

Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles

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...

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Main Authors: Xia, Mengxin, Lambu, Mallikharjuna Rao, Judeh, Zaher M. A.
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2022
Subjects:
Engineering::Chemical engineering
Cascade Reactions
Embeddings
Online Access:https://hdl.handle.net/10356/163328
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1633282022-12-02T05:56:51Z Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles Xia, Mengxin Lambu, Mallikharjuna Rao Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Chemical engineering Cascade Reactions Embeddings 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. Nanyang Technological University We thank Nanyang Technological University, Singapore, for the start-up grant. 2022-12-02T05:56:51Z 2022-12-02T05:56:51Z 2022 Journal Article 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 0022-3263 https://hdl.handle.net/10356/163328 10.1021/acs.joc.2c01270 2-s2.0-85137498970 18 87 12115 12131 en NTU-SUG Journal of Organic Chemistry © 2022 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Engineering::Chemical engineering
Cascade Reactions
Embeddings
spellingShingle Engineering::Chemical engineering
Cascade Reactions
Embeddings
Xia, Mengxin
Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
description 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.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
Xia, Mengxin
Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
format Article
author Xia, Mengxin
Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
author_sort Xia, Mengxin
title Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
title_short Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
title_full Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
title_fullStr Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
title_full_unstemmed Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
title_sort selective one-pot cascade synthesis of n-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
publishDate 2022
url https://hdl.handle.net/10356/163328
_version_ 1751548571434352640

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