One-Pot Synthesis of Pentasubstituted Pyridines following the Gold(I)-Catalyzed Aza-Enyne Metathesis/6π-Electrocyclization-Aromatization Sequence

Shuto Kosuge; Yusuke Araki; Kiyoshi Tsuge; Kenji Sugimoto; Yuji Matsuya

doi:10.1021/acs.joc.3c00270

One-Pot Synthesis of Pentasubstituted Pyridines following the Gold(I)-Catalyzed Aza-Enyne Metathesis/6π-Electrocyclization-Aromatization Sequence

Shuto Kosuge, Yusuke Araki, Kiyoshi Tsuge, Kenji Sugimoto^*, Yuji Matsuya^*

^*Corresponding author for this work

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

4 Scopus citations

Abstract

The one-pot de novo synthesis of pentasubstituted pyridines was realized following the process of Au(I)-autotandem catalysis and subsequent aromatization. The process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6π-electrocyclization sequence with the other propiolate units. The resultant 1,4-dihydropyridines were aromatized to furnish the pyridines in the presence of atmospheric oxygen. The aryl propiolates were regioselectively incorporated into the ring system to afford 2-arylpyridines as the sole product.

Original language	English
Pages (from-to)	6973-6986
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	88
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.3c00270
State	Published - 2023/06/02

ASJC Scopus subject areas

Organic Chemistry

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title = "One-Pot Synthesis of Pentasubstituted Pyridines following the Gold(I)-Catalyzed Aza-Enyne Metathesis/6π-Electrocyclization-Aromatization Sequence",

abstract = "The one-pot de novo synthesis of pentasubstituted pyridines was realized following the process of Au(I)-autotandem catalysis and subsequent aromatization. The process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6π-electrocyclization sequence with the other propiolate units. The resultant 1,4-dihydropyridines were aromatized to furnish the pyridines in the presence of atmospheric oxygen. The aryl propiolates were regioselectively incorporated into the ring system to afford 2-arylpyridines as the sole product.",

author = "Shuto Kosuge and Yusuke Araki and Kiyoshi Tsuge and Kenji Sugimoto and Yuji Matsuya",

year = "2023",

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doi = "10.1021/acs.joc.3c00270",

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T1 - One-Pot Synthesis of Pentasubstituted Pyridines following the Gold(I)-Catalyzed Aza-Enyne Metathesis/6π-Electrocyclization-Aromatization Sequence

AU - Kosuge, Shuto

AU - Araki, Yusuke

AU - Tsuge, Kiyoshi

AU - Sugimoto, Kenji

AU - Matsuya, Yuji

PY - 2023/6/2

Y1 - 2023/6/2

N2 - The one-pot de novo synthesis of pentasubstituted pyridines was realized following the process of Au(I)-autotandem catalysis and subsequent aromatization. The process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6π-electrocyclization sequence with the other propiolate units. The resultant 1,4-dihydropyridines were aromatized to furnish the pyridines in the presence of atmospheric oxygen. The aryl propiolates were regioselectively incorporated into the ring system to afford 2-arylpyridines as the sole product.

AB - The one-pot de novo synthesis of pentasubstituted pyridines was realized following the process of Au(I)-autotandem catalysis and subsequent aromatization. The process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6π-electrocyclization sequence with the other propiolate units. The resultant 1,4-dihydropyridines were aromatized to furnish the pyridines in the presence of atmospheric oxygen. The aryl propiolates were regioselectively incorporated into the ring system to afford 2-arylpyridines as the sole product.

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DO - 10.1021/acs.joc.3c00270

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SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

One-Pot Synthesis of Pentasubstituted Pyridines following the Gold(I)-Catalyzed Aza-Enyne Metathesis/6π-Electrocyclization-Aromatization Sequence

Abstract

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