Journal of Organic Chemistry, volume 82, issue 23, pages 12224-12237
Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles
Maozhong Miao
1
,
Luo Yi
1
,
Huaping Xu
1
,
Mengchao Jin
1
,
Zhengkai Chen
1
,
Jianfeng Xu
1
,
Hongjun Ren
1
Publication type: Journal Article
Publication date: 2017-10-30
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The tunable nucleophilic nitration of 3-cyclopropylideneprop-2-en-1-ones with cheap sodium nitrite is described. This transformation proceeds with the assistance of a strained cyclopropane ring and allows for a divergent route to various synthetically useful β,γ-dinitro or γ-mononitro adducts in high yields with exclusive regio- and stereoselectivity. Additionally, a wide array of valuable functionalized N-unprotected pyrroles is achieved from the resulting β,γ-dinitro compounds via reductive cyclization strategy.
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Miao M. et al. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles // Journal of Organic Chemistry. 2017. Vol. 82. No. 23. pp. 12224-12237.
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Miao M., Yi L., Xu H., Jin M., Chen Z., Xu J., Ren H. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles // Journal of Organic Chemistry. 2017. Vol. 82. No. 23. pp. 12224-12237.
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TY - JOUR
DO - 10.1021/acs.joc.7b02087
UR - https://doi.org/10.1021/acs.joc.7b02087
TI - Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles
T2 - Journal of Organic Chemistry
AU - Miao, Maozhong
AU - Yi, Luo
AU - Xu, Huaping
AU - Jin, Mengchao
AU - Chen, Zhengkai
AU - Xu, Jianfeng
AU - Ren, Hongjun
PY - 2017
DA - 2017/10/30
PB - American Chemical Society (ACS)
SP - 12224-12237
IS - 23
VL - 82
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Miao,
author = {Maozhong Miao and Luo Yi and Huaping Xu and Mengchao Jin and Zhengkai Chen and Jianfeng Xu and Hongjun Ren},
title = {Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.7b02087},
number = {23},
pages = {12224--12237},
doi = {10.1021/acs.joc.7b02087}
}
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Miao, Maozhong, et al. “Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles.” Journal of Organic Chemistry, vol. 82, no. 23, Oct. 2017, pp. 12224-12237. https://doi.org/10.1021/acs.joc.7b02087.