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Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides

Tatiana Aleksandrovna Solodovnikova 1
Tatiana Aleksandrovna Solodovnikova
Nikolai Vasil'evich Zyk 1
Nikolai Vasil'evich Zyk
Anna Yuryevna Gavrilova 1
Anna Yuryevna Gavrilova
Published 2022-07-01
CommunicationVolume 32, Issue 4, 549-550
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Solodovnikova T. A., Zyk N. V., Gavrilova A. Y. Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 549-550.
GOST all authors (up to 50) Copy
Solodovnikova T. A., Zyk N. V., Gavrilova A. Y. Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 549-550.
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TY - JOUR
DO - 10.1016/j.mencom.2022.07.038
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.038
TI - Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides
T2 - Mendeleev Communications
AU - Solodovnikova, Tatiana Aleksandrovna
AU - Zyk, Nikolai Vasil'evich
AU - Gavrilova, Anna Yuryevna
PY - 2022
DA - 2022/07/01
PB - Mendeleev Communications
SP - 549-550
IS - 4
VL - 32
ER -
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@article{2022_Solodovnikova,
author = {Tatiana Aleksandrovna Solodovnikova and Nikolai Vasil'evich Zyk and Anna Yuryevna Gavrilova},
title = {Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.038},
number = {4},
pages = {549--550},
doi = {10.1016/j.mencom.2022.07.038}
}
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Solodovnikova, Tatiana Aleksandrovna, et al. “Reaction of 2-azabicyclo[2.2.1]heptenes with nitrile oxides.” Mendeleev Communications, vol. 32, no. 4, Jul. 2022, pp. 549-550. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.038.

Keywords

13-dipolar cycloaddition
2-azabicyclo[2.2.1]heptanes
hydroxyimoyl halides
isoxazolines
nitrile oxides
norbornene

Abstract

The reaction of 2-azanorbornene derivatives with nitrile oxides (generated in situ by dehydrohalogenation of N-hydroxyimoyl halides) affords two regioisomers with the exo-arrangement of the isoxazoline ring.

References

1.
2-Azanorbornane – a versatile chiral aza-Diels–Alder cycloadduct: preparation, applications in stereoselective synthesis and biological activity
Wojaczyńska E., Wojaczyński J., Kleniewska K., Dorsz M., Olszewski T.K.
Organic and Biomolecular Chemistry, 2015
2.
The isoxazoline route to the molecules of nature
Kozikowski A.P.
Accounts of Chemical Research, 1984
4.
1,3-Dipolare Cycloadditionen der Knallsäure
Huisgen R., Christl M.
Angewandte Chemie, 1967
6.
Simple in situ preparation of fulmimic acid
De Sarlo(rk) F., Brandi A., Guarna A., Goti A., Corezzi S.
Tetrahedron Letters, 1983
7.
The chemistry of fulminic acid revised
de Sarlo F., Guarna A., Brandi A., Goti A.
Tetrahedron, 1985
8.
Conversion of isoxazolines to β-hydroxy esters. Synthesis of 2-deoxy-D-ribose
Caldirola P., Ciancaglione M., De Amici M., De Micheli C.
Tetrahedron Letters, 1986
9.
Exceptional reactivity of the bicyclo[2.2.1]heptene double bond
Huisgen R., Ooms P.H., Mingin M., Allinger N.L.
Journal of the American Chemical Society, 1980
11.
O-Trimethylsilyl hydroxamoyl chlorides as nitrile oxide precursors
Cunico R.F., Bedell L.
Journal of Organic Chemistry, 1983
12.
10.1016/j.mencom.2022.07.038_b0060
Cecchi
Synlett, 2007
14.
Pathways in the reactions of nitronate ions with sulphonyl halides
Pigou P.E., Stirling C.J.
Journal of the Chemical Society Perkin Transactions 2, 1988
16.
[2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines
Ma L., Jin F., Cheng X., Tao S., Jiang G., Li X., Yang J., Bao X., Wan X.
Chemical Science, 2021
17.
Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.
Mendelsohn B.A., Lee S., Kim S., Teyssier F., Aulakh V.S., Ciufolini M.A.
Organic Letters, 2009
19.
Oxidation of α-oxo-oximes to nitrile oxides with hypervalent iodine reagents.
Jen T., Mendelsohn B.A., Ciufolini M.A.
Journal of Organic Chemistry, 2010
20.
Beyond azide-alkyne click reaction: easy access to 18F-labelled compounds via nitrile oxide cycloadditions.
Zlatopolskiy B.D., Kandler R., Kobus D., Mottaghy F.M., Neumaier B.
Chemical Communications, 2012
25.
10.1016/j.mencom.2022.07.038_b0125
Gucma
J. Braz. Chem. Soc., 2016
26.
Bicyclic γ-amino acids as inhibitors of γ-aminobutyrate aminotransferase
Pinto A., Tamborini L., Pennacchietti E., Coluccia A., Silvestri R., Cullia G., De Micheli C., Conti P., De Biase D.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2015
28.
Peramivir analogues bearing hydrophilic side chains exhibit higher activities against H275Y mutant than wild-type influenza virus
Chiu D., Lin T., Huang W., Cheng T., Tsai K., Fang J.
Organic and Biomolecular Chemistry, 2017
30.
Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels–Alder reactions
Quadrelli P., Piccanello A., Martinez N.V., Bovio B., Mella M., Caramella P.
Tetrahedron, 2006
32.
10.1016/j.mencom.2022.07.038_b0160
Khmelnitsky
Khimiya furoksanov: stroenie i svoistva (Chemistry of Furoxans: Structure and Properties), 1996
33.
10.1016/j.mencom.2022.07.038_b0165
Gordon
The Chemist’s Companion, 1972
34.
O. A. Reutov, A. L. Kurts and K. P. Butin, Organicheskaya khimiya (Organic Chemistry), Binom. Laboratoriya znanii, Moscow, 2004, vol. 3 (in Russian).