Tandem Blaise-Nenitzescu reaction: One-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles

Yu Sung Chun; Ka Yeon Ryu; Ju Hyun Kim; Hyunik Shin; Sang Gi Lee

doi:10.1039/c0ob01024c

Tandem Blaise-Nenitzescu reaction: One-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles

Yu Sung Chun, Ka Yeon Ryu, Ju Hyun Kim, Hyunik Shin, Sang Gi Lee

Department of Chemistry & Nanoscience

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

24 Scopus citations

Abstract

In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise-Nenitzescu reaction).

Original language	English
Pages (from-to)	1317-1319
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	5
DOIs	https://doi.org/10.1039/c0ob01024c
State	Published - 1 Mar 2011

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title = "Tandem Blaise-Nenitzescu reaction: One-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles",

abstract = "In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise-Nenitzescu reaction).",

author = "Chun, {Yu Sung} and Ryu, {Ka Yeon} and Kim, {Ju Hyun} and Hyunik Shin and Lee, {Sang Gi}",

year = "2011",

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doi = "10.1039/c0ob01024c",

language = "English",

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journal = "Organic and Biomolecular Chemistry",

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T1 - Tandem Blaise-Nenitzescu reaction

T2 - One-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles

AU - Chun, Yu Sung

AU - Ryu, Ka Yeon

AU - Kim, Ju Hyun

AU - Shin, Hyunik

AU - Lee, Sang Gi

PY - 2011/3/1

Y1 - 2011/3/1

N2 - In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise-Nenitzescu reaction).

AB - In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise-Nenitzescu reaction).

UR - http://www.scopus.com/inward/record.url?scp=79951650211&partnerID=8YFLogxK

U2 - 10.1039/c0ob01024c

DO - 10.1039/c0ob01024c

M3 - Article

C2 - 21212872

AN - SCOPUS:79951650211

SN - 1477-0520

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SP - 1317

EP - 1319

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 5

ER -

Tandem Blaise-Nenitzescu reaction: One-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles

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