Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
Yulia Volkova
1
,
E. B. Averina
1
,
Kseniya N. Sedenkova
1
,
Yuri K. Grishin
1
,
Per Bruheim
2
,
Tamara S. Kuznetsova
1
,
Nikolai S. Zefirov
1
Publication type: Journal Article
Publication date: 2019-02-06
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30726081
Organic Chemistry
Abstract
A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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GOST
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Volkova Y. et al. Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles // Journal of Organic Chemistry. 2019. Vol. 84. No. 6. pp. 3192-3200.
GOST all authors (up to 50)
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Volkova Y., Averina E. B., Vasilenko D. A., Sedenkova K. N., Grishin Y. K., Bruheim P., Kuznetsova T. S., Zefirov N. S. Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles // Journal of Organic Chemistry. 2019. Vol. 84. No. 6. pp. 3192-3200.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.8b03086
UR - https://doi.org/10.1021/acs.joc.8b03086
TI - Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
T2 - Journal of Organic Chemistry
AU - Volkova, Yulia
AU - Averina, E. B.
AU - Vasilenko, Dmitry A.
AU - Sedenkova, Kseniya N.
AU - Grishin, Yuri K.
AU - Bruheim, Per
AU - Kuznetsova, Tamara S.
AU - Zefirov, Nikolai S.
PY - 2019
DA - 2019/02/06
PB - American Chemical Society (ACS)
SP - 3192-3200
IS - 6
VL - 84
PMID - 30726081
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Volkova,
author = {Yulia Volkova and E. B. Averina and Dmitry A. Vasilenko and Kseniya N. Sedenkova and Yuri K. Grishin and Per Bruheim and Tamara S. Kuznetsova and Nikolai S. Zefirov},
title = {Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.joc.8b03086},
number = {6},
pages = {3192--3200},
doi = {10.1021/acs.joc.8b03086}
}
Cite this
MLA
Copy
Volkova, Yulia, et al. “Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.” Journal of Organic Chemistry, vol. 84, no. 6, Feb. 2019, pp. 3192-3200. https://doi.org/10.1021/acs.joc.8b03086.