A facile synthesis of gem-difluorinated heterocyclic compounds using anodic fluorination of 2-cyano-1-methylpyrrole as a key step

Toshiki Tajima; Toshio Fuchigami

doi:10.1055/s-2002-35621

A facile synthesis of gem-difluorinated heterocyclic compounds using anodic fluorination of 2-cyano-1-methylpyrrole as a key step

Toshiki Tajima, Toshio Fuchigami

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

10 Citations (Scopus)

Abstract

Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et₃N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.

Original language	English
Pages (from-to)	2597-2600
Number of pages	4
Journal	Synthesis
Issue number	17
DOIs	https://doi.org/10.1055/s-2002-35621
Publication status	Published - 2002
Externally published	Yes

Keywords

5,5-difluoro-1-methyl-3-pyrroline-2-one
Anodic fluorination
Diels-Alder reaction
Dienes
gem-difluoromethylenes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2002-35621

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title = "A facile synthesis of gem-difluorinated heterocyclic compounds using anodic fluorination of 2-cyano-1-methylpyrrole as a key step",

abstract = "Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et3N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.",

keywords = "5,5-difluoro-1-methyl-3-pyrroline-2-one, Anodic fluorination, Diels-Alder reaction, Dienes, gem-difluoromethylenes",

author = "Toshiki Tajima and Toshio Fuchigami",

year = "2002",

doi = "10.1055/s-2002-35621",

language = "English",

pages = "2597--2600",

journal = "Synthesis",

issn = "0039-7881",

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T1 - A facile synthesis of gem-difluorinated heterocyclic compounds using anodic fluorination of 2-cyano-1-methylpyrrole as a key step

AU - Tajima, Toshiki

AU - Fuchigami, Toshio

PY - 2002

Y1 - 2002

N2 - Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et3N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.

AB - Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et3N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.

KW - 5,5-difluoro-1-methyl-3-pyrroline-2-one

KW - Anodic fluorination

KW - Diels-Alder reaction

KW - Dienes

KW - gem-difluoromethylenes

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DO - 10.1055/s-2002-35621

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SN - 0039-7881

SP - 2597

EP - 2600

JO - Synthesis

JF - Synthesis

IS - 17

ER -

A facile synthesis of gem-difluorinated heterocyclic compounds using anodic fluorination of 2-cyano-1-methylpyrrole as a key step

Abstract

Keywords

ASJC Scopus subject areas

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