Home / Publications / [4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones

[4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones

Gulnara Nazifovna Kadikova 1
Gulnara Nazifovna Kadikova
, 
Ekaterina Sergeevna Meshcheryakova 1
Ekaterina Sergeevna Meshcheryakova
, 
Leonard Mukhibovich Khalilov 1
Leonard Mukhibovich Khalilov
1 Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2023.10.036
Published 2023-10-18
Communication , Volume 33, Issue 6, 847-849
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Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. [4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 847-849.
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Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. [4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 847-849.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.036
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.036
TI - [4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones
T2 - Mendeleev Communications
AU - Kadikova, Gulnara Nazifovna
AU - Meshcheryakova, Ekaterina Sergeevna
AU - Khalilov, Leonard Mukhibovich
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 847-849
IS - 6
VL - 33
ER -
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@article{2023_Kadikova,
author = {Gulnara Nazifovna Kadikova and Ekaterina Sergeevna Meshcheryakova and Leonard Mukhibovich Khalilov},
title = {[4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.036},
number = {6},
pages = {847--849},
doi = {10.1016/j.mencom.2023.10.036}
}
MLA
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Kadikova, Gulnara Nazifovna, et al. “[4 + 2]-Cycloaddition of maleic anhydride to substituted cycloheptatrienes for the synthesis of novel 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 847-849. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.036.

Keywords

10]dodec-11-ene-35-diones
3
4-oxatetracyclo[5.3.2.02
5-cycloheptatrienes
6.08
7-substituted 1
biologically active compounds.
cycloaddition
maleic anhydride

Abstract

The [4+2]-cycloaddition of maleic anhydride to 7-substituted 1,3,5-cycloheptatrienes involves their 7-R-bicyclo[4.1.0]-hepta-2,4-diene tautomers and affords new 4-oxatetra- cyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones in 85-95% yields. The structure of the resulting adducts is proved using advanced 1D and 2D NMR techniques and X-ray diffraction analysis. The cycloaddition proceeds stereo specifically providing meso-(1S*,2S*,6R*,7R*,8R*,9-anti,10S*)-configuration in the products

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