Zn(OTf)2-Promoted Isocyanide-Based Three-Component Reaction: Direct Access to 2-Oxazolines and β-Amino Amides

Jie Lei; Shi Qiang Li; Ya Fei Luo; Dian Yong Tang; Cheng He Zhou; Hong Yu Li; Zhi Gang Xu; Zhong Zhu Chen

doi:10.1021/acs.joc.2c01437

Zn(OTf)₂-Promoted Isocyanide-Based Three-Component Reaction: Direct Access to 2-Oxazolines and β-Amino Amides

Jie Lei, Shi Qiang Li, Ya Fei Luo, Dian Yong Tang, Cheng He Zhou, Hong Yu Li, Zhi Gang Xu, Zhong Zhu Chen

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

An efficient one-pot reaction of propargylamides, isocyanides, and water catalyzed by zinc was developed for the rapid construction of 2-oxazolines with a wide functional group tolerance. The methylene-3-oxazoline was proven to play a vitally important role to start the tandem cascade transformation through unfunctionalized alkynes with sequential nucleophilic addition approaches of isocyanide and water. Notably, with a slight alteration of the reaction temperature and the addition of one molecule of water, various β-amino amide derivatives were synthesized in good to excellent yields.

Original language	English (US)
Pages (from-to)	11888-11898
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	87
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.2c01437
State	Published - Sep 2 2022
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.2c01437

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title = "Zn(OTf)2-Promoted Isocyanide-Based Three-Component Reaction: Direct Access to 2-Oxazolines and β-Amino Amides",

abstract = "An efficient one-pot reaction of propargylamides, isocyanides, and water catalyzed by zinc was developed for the rapid construction of 2-oxazolines with a wide functional group tolerance. The methylene-3-oxazoline was proven to play a vitally important role to start the tandem cascade transformation through unfunctionalized alkynes with sequential nucleophilic addition approaches of isocyanide and water. Notably, with a slight alteration of the reaction temperature and the addition of one molecule of water, various β-amino amide derivatives were synthesized in good to excellent yields.",

author = "Jie Lei and Li, {Shi Qiang} and Luo, {Ya Fei} and Tang, {Dian Yong} and Zhou, {Cheng He} and Li, {Hong Yu} and Xu, {Zhi Gang} and Chen, {Zhong Zhu}",

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doi = "10.1021/acs.joc.2c01437",

language = "English (US)",

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T1 - Zn(OTf)2-Promoted Isocyanide-Based Three-Component Reaction

T2 - Direct Access to 2-Oxazolines and β-Amino Amides

AU - Lei, Jie

AU - Li, Shi Qiang

AU - Luo, Ya Fei

AU - Tang, Dian Yong

AU - Zhou, Cheng He

AU - Li, Hong Yu

AU - Xu, Zhi Gang

AU - Chen, Zhong Zhu

PY - 2022/9/2

Y1 - 2022/9/2

N2 - An efficient one-pot reaction of propargylamides, isocyanides, and water catalyzed by zinc was developed for the rapid construction of 2-oxazolines with a wide functional group tolerance. The methylene-3-oxazoline was proven to play a vitally important role to start the tandem cascade transformation through unfunctionalized alkynes with sequential nucleophilic addition approaches of isocyanide and water. Notably, with a slight alteration of the reaction temperature and the addition of one molecule of water, various β-amino amide derivatives were synthesized in good to excellent yields.

AB - An efficient one-pot reaction of propargylamides, isocyanides, and water catalyzed by zinc was developed for the rapid construction of 2-oxazolines with a wide functional group tolerance. The methylene-3-oxazoline was proven to play a vitally important role to start the tandem cascade transformation through unfunctionalized alkynes with sequential nucleophilic addition approaches of isocyanide and water. Notably, with a slight alteration of the reaction temperature and the addition of one molecule of water, various β-amino amide derivatives were synthesized in good to excellent yields.

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Zn(OTf)₂-Promoted Isocyanide-Based Three-Component Reaction: Direct Access to 2-Oxazolines and β-Amino Amides

Abstract

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