Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation
Gang Chen
1
,
Guangjie Nie
1
,
Linxuan Li
1, 2
,
Jie Fu
1
,
Hui Yao
1, 2
,
Nianyu Huang
1, 2
,
Nengzhong Wang
1, 2
2
Hubei Three Gorges Laboratory, Yichang Hubei 443007, China
|
Publication type: Journal Article
Publication date: 2025-01-22
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Abstract
Annulation reactions are recognized for their efficiency in constructing complex cyclic compounds with multiple substitutions, aligning well with green chemistry principles. Herein, we report a transition-metal-free, chemodiverse cycloaddition reaction employing allylamines as [C,N] synthons that react with azadienes in an environmentally benign manner. The protocol has been applied to benzofuran- and indanone-derived azadienes via [3 + 2] cycloadditions, and to benzothiophene-derived azadienes via [3 + 4] cycloadditions, yielding a series of spirobenzofurans, spirotetrandrines, and benzothiophene-diazepines with high diastereoselectivity. In addition to avoiding the use of toxic transition metals, the process demonstrates the potential for further functional group transformations of the cycloaddition products, paving the way for the sustainable generation of valuable intermediates.
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8
Total citations:
8
Citations from 2024:
7
(87.5%)
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GOST
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Chen G. et al. Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation // Organic Chemistry Frontiers. 2025. Vol. 12. No. 7. pp. 2212-2218.
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Chen G., Nie G., Li L., Fu J., Yao H., Huang N., Wang N. Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation // Organic Chemistry Frontiers. 2025. Vol. 12. No. 7. pp. 2212-2218.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d4qo02400a
UR - http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02400A
TI - Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation
T2 - Organic Chemistry Frontiers
AU - Chen, Gang
AU - Nie, Guangjie
AU - Li, Linxuan
AU - Fu, Jie
AU - Yao, Hui
AU - Huang, Nianyu
AU - Wang, Nengzhong
PY - 2025
DA - 2025/01/22
PB - Royal Society of Chemistry (RSC)
SP - 2212-2218
IS - 7
VL - 12
SN - 2052-4110
SN - 2052-4129
ER -
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BibTex (up to 50 authors)
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@article{2025_Chen,
author = {Gang Chen and Guangjie Nie and Linxuan Li and Jie Fu and Hui Yao and Nianyu Huang and Nengzhong Wang},
title = {Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation},
journal = {Organic Chemistry Frontiers},
year = {2025},
volume = {12},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02400A},
number = {7},
pages = {2212--2218},
doi = {10.1039/d4qo02400a}
}
Cite this
MLA
Copy
Chen, Gang, et al. “Atom-controlled divergent synthesis of spiro and fused rings via base-catalyzed chemoselective annulation.” Organic Chemistry Frontiers, vol. 12, no. 7, Jan. 2025, pp. 2212-2218. http://pubs.rsc.org/en/Content/ArticleLanding/2025/QO/D4QO02400A.
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