Home / Publications / Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne

Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne

Evgenii Vladimirovich Shulishov 1
Evgenii Vladimirovich Shulishov
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
Published 2013-07-11
CommunicationVolume 23, Issue 4, 187-189
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Shulishov E. V., Tomilov Y. V., Nefedov O. M. Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne // Mendeleev Communications. 2013. Vol. 23. No. 4. pp. 187-189.
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Shulishov E. V., Tomilov Y. V., Nefedov O. M. Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne // Mendeleev Communications. 2013. Vol. 23. No. 4. pp. 187-189.
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TY - JOUR
DO - 10.1016/j.mencom.2013.07.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.002
TI - Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne
T2 - Mendeleev Communications
AU - Shulishov, Evgenii Vladimirovich
AU - Tomilov, Yury Vasil'evich
AU - Nefedov, Oleg Matveevich
PY - 2013
DA - 2013/07/11
PB - Mendeleev Communications
SP - 187-189
IS - 4
VL - 23
ER -
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@article{2013_Shulishov,
author = {Evgenii Vladimirovich Shulishov and Yury Vasil'evich Tomilov and Oleg Matveevich Nefedov},
title = {Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.002},
number = {4},
pages = {187--189},
doi = {10.1016/j.mencom.2013.07.002}
}
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Shulishov, Evgenii Vladimirovich, et al. “Annelated 4,5-diazaspiro[2.4]hepta-4,6-diene obtained by [3 + 2] Cycloaddition of Diazocyclopropane to Cyclooctyne.” Mendeleev Communications, vol. 23, no. 4, Jul. 2013, pp. 187-189. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.002.

Abstract

The 1,3-dipolar cycloaddition of diazocyclopropane generated in situ to cyclooctyne at –30 to –25°C afforded highly reactive spiro(9,10-diazabicyclo[6.3.0]undeca-1(8),9-diene-11,1’-cyclopropane) which can add nucleophiles to the azocyclopropane fragment or undergo oligomerization with three-membered ring opening.

References

2.
Synthesis and thermal transformations of pyrazolines obtained by 1,3-dipolar addition of diazocyclopropane to maleimides
Kostyuchenko I.V., Shulishov E.V., Rafikov R.R., Tomilov Y.V.
Russian Chemical Bulletin, 2008
4.
Reaction of levoglucosenone with diazocyclopropane
Rafikov R.R., Novikov R.A., Shulishov E.V., Konyushkin L.D., Semenov V.V., Tomilov Y.V.
Russian Chemical Bulletin, 2009
6.
Zur Existenz niedergliedriger Cycloalkine, I
Wittig G., Krebs A.
Chemische Berichte, 1961
7.
An Improved Synthesis of Cyclooctyne
BRANDSMA L., VERKRUIJSSE H.D.
Synthesis, 1978
8.
Hemilabile Ligands in Organolithium Chemistry:  Substituent Effects on Lithium Ion Chelation
Ramírez A., Lobkovsky E., Collum D.B.
Journal of the American Chemical Society, 2003
9.
Lithium Diisopropylamide Solvated by Hexamethylphosphoramide:  Substrate-Dependent Mechanisms for Dehydrobrominations
Ma Y., Ramirez A., Singh K.J., Keresztes I., Collum D.B.
Journal of the American Chemical Society, 2006
10.
1,3‐Dipolare Cycloadditionen bei Cycloalkeninen
König P., Zountsas J., Bleckmann K., Meier H.
Chemische Berichte, 1983
12.
Rearrangements and cyclization-XVII
Zefirov N.S., Kozhushkov S.I., Kuznetsova T.S., Ershov B.A., Selivanov S.I.
Tetrahedron, 1986
13.
3-Pyrazolone analogues of the 3-isoxazolol metabotropic excitatory amino acid receptor agonist homo-AMPA. Synthesis and pharmacological testing
Zimmermann D., Janin Y.L., Brehm L., Bräuner-Osborne H., Ebert B., Johansen T.N., Madsen U., Krogsgaard-Larsen P.
European Journal of Medicinal Chemistry, 1999