Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes
Publication type: Journal Article
Publication date: 2022-01-20
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
35049314
Organic Chemistry
Abstract
The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction of 2-imidazolines with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, containing an N-vinylpropargylamine fragment. The latter can then undergo a base-catalyzed domino aza-Claisen rearrangement/cyclization reaction sequence, simultaneously constructing pyrrole and pyrazine rings. The process works in a broad substrate scope, delivering pyrrolo[1,2-a]pyrazines in good to excellent yields (45-90%). This two-step approach can be carried out in a one-pot fashion without a noticeable decrease in yield. Remarkably, a three-component protocol for the introduction of two different alkynes has been also developed.
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9
Total citations:
9
Citations from 2024:
4
(44.44%)
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Golantsov N. E. et al. Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 3242-3253.
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Golantsov N. E., Golubenkova A. S., Festa A. A., Varlamov A. V., Voskressensky L. G. Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 3242-3253.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.1c02930
UR - https://doi.org/10.1021/acs.joc.1c02930
TI - Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes
T2 - Journal of Organic Chemistry
AU - Golantsov, Nikita E
AU - Golubenkova, Alexandra S
AU - Festa, Alexey A.
AU - Varlamov, Alexey V
AU - Voskressensky, Leonid G.
PY - 2022
DA - 2022/01/20
PB - American Chemical Society (ACS)
SP - 3242-3253
IS - 5
VL - 87
PMID - 35049314
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Golantsov,
author = {Nikita E Golantsov and Alexandra S Golubenkova and Alexey A. Festa and Alexey V Varlamov and Leonid G. Voskressensky},
title = {Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.joc.1c02930},
number = {5},
pages = {3242--3253},
doi = {10.1021/acs.joc.1c02930}
}
Cite this
MLA
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Golantsov, Nikita E., et al. “Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes.” Journal of Organic Chemistry, vol. 87, no. 5, Jan. 2022, pp. 3242-3253. https://doi.org/10.1021/acs.joc.1c02930.