Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones
Publication type: Journal Article
Publication date: 2022-11-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36321357
Organic Chemistry
Abstract
A novel protocol for the construction of highly functionalized indolizine derivatives, that is, 1H-pyrrolo[3,4-b]indolizine-1,3-diones (PIZDOs, 3) from 2-(pyridine-2-yl)acetates and maleimides via a regioselective oxidative [3 + 2] annulation was developed. The cascade oxidative reaction was enabled by heating a mixture of the two substrates in the presence of Ag2CO3 as an oxidant and Cu(OAc)·H2O as a catalyst in chlorobenzene. Consequently, a series of PIZDOs 3 were synthesized with high regioselectivity in moderate yields. This protocol can be used in the synthesis of functionalized PIZDOs via the one-pot oxidative annulation reaction rather than through multistep reactions, which is suitable for both combinatorial and parallel syntheses of PIZDOs.
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12
Total citations:
12
Citations from 2024:
10
(83.34%)
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Lv K. H. et al. Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones // Journal of Organic Chemistry. 2022. Vol. 87. No. 22. pp. 15301-15311.
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Lv K. H., Zhao Q. S., Zhao K. H., Yang J., Yan S. Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones // Journal of Organic Chemistry. 2022. Vol. 87. No. 22. pp. 15301-15311.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.2c01879
UR - https://doi.org/10.1021/acs.joc.2c01879
TI - Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones
T2 - Journal of Organic Chemistry
AU - Lv, Kai Hong
AU - Zhao, Qing Sheng
AU - Zhao, Ke Hua
AU - Yang, Jia-Ming
AU - Yan, Shengjiao
PY - 2022
DA - 2022/11/02
PB - American Chemical Society (ACS)
SP - 15301-15311
IS - 22
VL - 87
PMID - 36321357
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Lv,
author = {Kai Hong Lv and Qing Sheng Zhao and Ke Hua Zhao and Jia-Ming Yang and Shengjiao Yan},
title = {Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.2c01879},
number = {22},
pages = {15301--15311},
doi = {10.1021/acs.joc.2c01879}
}
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MLA
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Lv, Kai Hong, et al. “Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones.” Journal of Organic Chemistry, vol. 87, no. 22, Nov. 2022, pp. 15301-15311. https://doi.org/10.1021/acs.joc.2c01879.