Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones
Publication type: Journal Article
Publication date: 2017-07-11
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A concise transition-metal-free strategy for the synthesis of pyrrolo[1,2-a]pyrazines with enone substituents has been developed. It includes the following key steps: (a) cross-coupling of pyrroles with acyl(bromo)acetylenes in solid alumina at room temperature to give 2-(acylethynyl)pyrroles; (b) addition of propargylamine to the above acetylenes to form the corresponding N-propargylenaminones; and (c) chemo- and stereoselective base-catalyzed (Cs2CO3/DMSO) intramolecular cyclization of the synthesized propargylic derivatives to form (acylmethylidene)pyrrolo[1,2-a]pyrazines of Z-configuration.
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GOST
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Sobenina L. et al. Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones // Synthesis. 2017. Vol. 49. No. 17. pp. 4065-4081.
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Sobenina L., Sagitova E., Ushakov I., Trofimov B. Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones // Synthesis. 2017. Vol. 49. No. 17. pp. 4065-4081.
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TY - JOUR
DO - 10.1055/s-0036-1588454
UR - https://doi.org/10.1055/s-0036-1588454
TI - Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones
T2 - Synthesis
AU - Sobenina, Lyubov
AU - Sagitova, Elena
AU - Ushakov, Igor
AU - Trofimov, Boris
PY - 2017
DA - 2017/07/11
PB - Georg Thieme Verlag KG
SP - 4065-4081
IS - 17
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Sobenina,
author = {Lyubov Sobenina and Elena Sagitova and Igor Ushakov and Boris Trofimov},
title = {Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones},
journal = {Synthesis},
year = {2017},
volume = {49},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-0036-1588454},
number = {17},
pages = {4065--4081},
doi = {10.1055/s-0036-1588454}
}
Cite this
MLA
Copy
Sobenina, Lyubov, et al. “Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones.” Synthesis, vol. 49, no. 17, Jul. 2017, pp. 4065-4081. https://doi.org/10.1055/s-0036-1588454.