Synthesis, volume 52, issue 18, pages 2667-2678
Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans
Publication type: Journal Article
Publication date: 2020-05-05
Catalysis
Organic Chemistry
Abstract
A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.
Citations by journals
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1
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Synthesis
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1 publication, 12.5%
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Asian Journal of Organic Chemistry
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1 publication, 12.5%
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Progress in Heterocyclic Chemistry
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Progress in Heterocyclic Chemistry
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1
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Citations by publishers
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1
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3
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Wiley
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Wiley
3 publications, 37.5%
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Elsevier
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Elsevier
2 publications, 25%
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Thieme
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Thieme
1 publication, 12.5%
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Springer Nature
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Springer Nature
1 publication, 12.5%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 12.5%
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- We do not take into account publications that without a DOI.
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Fershtat L. L. et al. Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans // Synthesis. 2020. Vol. 52. No. 18. pp. 2667-2678.
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Fershtat L. L., Chaplygin D. A., Ananyev I. V., Makhova N. N. Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans // Synthesis. 2020. Vol. 52. No. 18. pp. 2667-2678.
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TY - JOUR
DO - 10.1055/s-0040-1707393
UR - https://doi.org/10.1055%2Fs-0040-1707393
TI - Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans
T2 - Synthesis
AU - Fershtat, Leonid L.
AU - Chaplygin, Daniil A
AU - Ananyev, Ivan V.
AU - Makhova, Nina N
PY - 2020
DA - 2020/05/05 00:00:00
PB - Thieme
SP - 2667-2678
IS - 18
VL - 52
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2020_Fershtat,
author = {Leonid L. Fershtat and Daniil A Chaplygin and Ivan V. Ananyev and Nina N Makhova},
title = {Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans},
journal = {Synthesis},
year = {2020},
volume = {52},
publisher = {Thieme},
month = {may},
url = {https://doi.org/10.1055%2Fs-0040-1707393},
number = {18},
pages = {2667--2678},
doi = {10.1055/s-0040-1707393}
}
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MLA
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Fershtat, Leonid L., et al. “Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans.” Synthesis, vol. 52, no. 18, May. 2020, pp. 2667-2678. https://doi.org/10.1055%2Fs-0040-1707393.