Organic Letters, volume 14, issue 20, pages 5196-5199
[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines
Publication type: Journal Article
Publication date: 2012-10-01
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Two novel routes based on [5C + 1N] annulations for the synthesis of 2,3-dihydrofuro[3,2-c]pyridines are described. Ammonium acetate (NH(4)OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl]cyclopropanes as a five-carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dimethylamino)alkenyl]-4,5-dihydrofurans as the five-carbon synthons, which involves a sequential intermolecular aza-addition, intramolecular aza-nucleophilic addition/elimination, and dehydration reaction.
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Citations by publishers
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8
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8 publications, 29.63%
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1 publication, 3.7%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Huang P. et al. [5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines // Organic Letters. 2012. Vol. 14. No. 20. pp. 5196-5199.
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Huang P., Zhang R., Liang Y., Dong D. [5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines // Organic Letters. 2012. Vol. 14. No. 20. pp. 5196-5199.
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TY - JOUR
DO - 10.1021/ol302314c
UR - https://doi.org/10.1021/ol302314c
TI - [5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines
T2 - Organic Letters
AU - Liang, Yongjiu
AU - Dong, Dewen
AU - Huang, Peng
AU - Zhang, Rui
PY - 2012
DA - 2012/10/01 00:00:00
PB - American Chemical Society (ACS)
SP - 5196-5199
IS - 20
VL - 14
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2012_Huang,
author = {Yongjiu Liang and Dewen Dong and Peng Huang and Rui Zhang},
title = {[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines},
journal = {Organic Letters},
year = {2012},
volume = {14},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/ol302314c},
number = {20},
pages = {5196--5199},
doi = {10.1021/ol302314c}
}
Cite this
MLA
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Huang, Peng, et al. “[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines.” Organic Letters, vol. 14, no. 20, Oct. 2012, pp. 5196-5199. https://doi.org/10.1021/ol302314c.