One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit

Jeong Hwa Lee; Seok Hyun Yoon; Seonghyeon Nam; Ikyon Kim

doi:10.1039/d1ob00885d

One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit

Jeong Hwa Lee, Seok Hyun Yoon, Seonghyeon Nam, Ikyon Kim

Department of Pharmacy

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

1 Citation (Scopus)

Abstract

A new pyrrolo[1,2-a]pyrazine chemical space with a poly-substituted pyrazine unit was readily accessed by Sc(OTf)₃-catalyzed one-pot three-component coupling of a pyrrole derivative, amine, and trialkylphosphite under environment-friendly conditions. The formation of multiple bonds (two C-N and one C-P)viaa domino process consisting of the chemoselective Kabachnik-Fields reaction and intramolecular cyclodehydration allowed for the construction of highly functionalized pyrazines.

Original language	English
Pages (from-to)	6066-6084
Number of pages	19
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	27
DOIs	https://doi.org/10.1039/d1ob00885d
Publication status	Published - 2021 Jul 21

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.

Publisher Copyright:
© The Royal Society of Chemistry 2021.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d1ob00885d

Cite this

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abstract = "A new pyrrolo[1,2-a]pyrazine chemical space with a poly-substituted pyrazine unit was readily accessed by Sc(OTf)3-catalyzed one-pot three-component coupling of a pyrrole derivative, amine, and trialkylphosphite under environment-friendly conditions. The formation of multiple bonds (two C-N and one C-P)viaa domino process consisting of the chemoselective Kabachnik-Fields reaction and intramolecular cyclodehydration allowed for the construction of highly functionalized pyrazines.",

author = "Lee, {Jeong Hwa} and Yoon, {Seok Hyun} and Seonghyeon Nam and Ikyon Kim",

note = "Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

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doi = "10.1039/d1ob00885d",

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AU - Lee, Jeong Hwa

AU - Yoon, Seok Hyun

AU - Nam, Seonghyeon

AU - Kim, Ikyon

N1 - Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support. Publisher Copyright: © The Royal Society of Chemistry 2021.

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AB - A new pyrrolo[1,2-a]pyrazine chemical space with a poly-substituted pyrazine unit was readily accessed by Sc(OTf)3-catalyzed one-pot three-component coupling of a pyrrole derivative, amine, and trialkylphosphite under environment-friendly conditions. The formation of multiple bonds (two C-N and one C-P)viaa domino process consisting of the chemoselective Kabachnik-Fields reaction and intramolecular cyclodehydration allowed for the construction of highly functionalized pyrazines.

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One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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