Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines
Тип публикации: Journal Article
Дата публикации: 2021-05-21
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
34018747
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in the KOBut/DMSO solution to 2,3,5-triarylpyrrolines, which are oxidized (chloranil, DDQ) in situ to 2,3,5-triaryl-2H-pyrroles in 53-71% yields. The intermediate 1-pyrrolines can be isolated in 31-91% yields and separately oxidized to the corresponding 2H-pyrroles.
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Bidusenko I. A. et al. Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines // Organic Letters. 2021. Vol. 23. No. 11. pp. 4121-4126.
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Bidusenko I. A., Schmidt E. Yu., Ushakov I., Vashchenko A. V., Trofimov B. A. Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines // Organic Letters. 2021. Vol. 23. No. 11. pp. 4121-4126.
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TY - JOUR
DO - 10.1021/acs.orglett.1c01009
UR - https://doi.org/10.1021/acs.orglett.1c01009
TI - Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines
T2 - Organic Letters
AU - Bidusenko, Ivan A
AU - Schmidt, Elena Yu
AU - Ushakov, Igor
AU - Vashchenko, Alexander V.
AU - Trofimov, B. A.
PY - 2021
DA - 2021/05/21
PB - American Chemical Society (ACS)
SP - 4121-4126
IS - 11
VL - 23
PMID - 34018747
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2021_Bidusenko,
author = {Ivan A Bidusenko and Elena Yu Schmidt and Igor Ushakov and Alexander V. Vashchenko and B. A. Trofimov},
title = {Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.1c01009},
number = {11},
pages = {4121--4126},
doi = {10.1021/acs.orglett.1c01009}
}
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MLA
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Bidusenko, Ivan A., et al. “Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines.” Organic Letters, vol. 23, no. 11, May. 2021, pp. 4121-4126. https://doi.org/10.1021/acs.orglett.1c01009.
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