Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

Kenji Sugimoto; Shuto Kosuge; Takae Sugita; Yuka Miura; Kiyoshi Tsuge; Yuji Matsuya

doi:10.1021/acs.orglett.1c01171

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

Kenji Sugimoto^*, Shuto Kosuge, Takae Sugita, Yuka Miura, Kiyoshi Tsuge, Yuji Matsuya^*

^*Corresponding author for this work

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

6 Scopus citations

Abstract

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Original language	English
Pages (from-to)	3981-3985
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.1c01171
State	Published - 2021/05/21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization",

abstract = "A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.",

author = "Kenji Sugimoto and Shuto Kosuge and Takae Sugita and Yuka Miura and Kiyoshi Tsuge and Yuji Matsuya",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = may,

day = "21",

doi = "10.1021/acs.orglett.1c01171",

language = "英語",

volume = "23",

pages = "3981--3985",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

AU - Sugimoto, Kenji

AU - Kosuge, Shuto

AU - Sugita, Takae

AU - Miura, Yuka

AU - Tsuge, Kiyoshi

AU - Matsuya, Yuji

PY - 2021/5/21

Y1 - 2021/5/21

N2 - A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

AB - A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

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U2 - 10.1021/acs.orglett.1c01171

DO - 10.1021/acs.orglett.1c01171

M3 - 学術論文

C2 - 33979152

AN - SCOPUS:85106383485

SN - 1523-7060

VL - 23

SP - 3981

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JO - Organic Letters

JF - Organic Letters

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ER -

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

Abstract

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