One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit
THOMAS CHRISTOPH
1
,
Jeong Hwa Lee
2, 3, 4, 5
,
Seok Hyun Yoon
3, 4, 5, 6, 7
,
Seonghyeon Nam
1
,
Ikyon Kim
1, 2, 3, 4, 5
2
College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences
4
Incheon
|
5
Republic of Korea
|
7
Graduate Program of Industrial Pharmaceutical Sciences
Publication type: Journal Article
Publication date: 2021-06-10
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
34137765
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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) via a domino process consisting of the chemoselective Kabachnik-Fields reaction and intramolecular cyclodehydration allowed for the construction of highly functionalized pyrazines.
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Total citations:
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Citations from 2024:
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(77.77%)
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Lee J. H. et al. One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 27. pp. 6066-6084.
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CHRISTOPH T., Lee J. H., Yoon S. H., Nam S., Kim I. One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 27. pp. 6066-6084.
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RIS
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TY - JOUR
DO - 10.1039/d1ob00885d
UR - https://xlink.rsc.org/?DOI=D1OB00885D
TI - One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit
T2 - Organic and Biomolecular Chemistry
AU - CHRISTOPH, THOMAS
AU - Lee, Jeong Hwa
AU - Yoon, Seok Hyun
AU - Nam, Seonghyeon
AU - Kim, Ikyon
PY - 2021
DA - 2021/06/10
PB - Royal Society of Chemistry (RSC)
SP - 6066-6084
IS - 27
VL - 19
PMID - 34137765
SN - 1477-0520
SN - 1477-0539
ER -
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@article{2021_Lee,
author = {THOMAS CHRISTOPH and Jeong Hwa Lee and Seok Hyun Yoon and Seonghyeon Nam and Ikyon Kim},
title = {One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit},
journal = {Organic and Biomolecular Chemistry},
year = {2021},
volume = {19},
publisher = {Royal Society of Chemistry (RSC)},
month = {jun},
url = {https://xlink.rsc.org/?DOI=D1OB00885D},
number = {27},
pages = {6066--6084},
doi = {10.1039/d1ob00885d}
}
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MLA
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Lee, Jeong Hwa, et al. “One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit.” Organic and Biomolecular Chemistry, vol. 19, no. 27, Jun. 2021, pp. 6066-6084. https://xlink.rsc.org/?DOI=D1OB00885D.