Home / Publications / New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes

New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes

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
Published 2024-09-09
CommunicationVolume 34, Issue 5, 701-702
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 701-702.
GOST all authors (up to 50) Copy
Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 701-702.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.09.024
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.024
TI - New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes
T2 - Mendeleev Communications
AU - Kadikova, Gulnara Nazifovna
AU - Meshcheryakova, Ekaterina Sergeevna
AU - Khalilov, Leonard Mukhibovich
PY - 2024
DA - 2024/09/09
PB - Mendeleev Communications
SP - 701-702
IS - 5
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Kadikova,
author = {Gulnara Nazifovna Kadikova and Ekaterina Sergeevna Meshcheryakova and Leonard Mukhibovich Khalilov},
title = {New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.024},
number = {5},
pages = {701--702},
doi = {10.1016/j.mencom.2024.09.024}
}
MLA
Cite this
MLA Copy
Kadikova, Gulnara Nazifovna, et al. “New 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones via the cycloaddition of N-phenylmaleimide and cyclohepta-1,3,5-trienes.” Mendeleev Communications, vol. 34, no. 5, Sep. 2024, pp. 701-702. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.024.

Keywords

[4 + 2] cycloaddition
10]dodec-11-ene-3
3
4-azatetracyclo[5.3.2.02
5-diones
5-trienes
6.08
7-substituted cyclohepta-1
biologically active compounds.
diene adducts
N-phenylmaleimide

Abstract

The cycloaddition reactions of N-phenylmaleimide with 7-substituted cyclohepta-1,3,5-trienes afforded new 4-aza- tetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones in high yields (87-97%). The true substrates which underwent the [4 + 2] cycloaddition were the 7-R-bicyclo[4.1.0]hepta-2,4-diene tautomers. The structures of the synthesized compounds were proved by NMR spectroscopy and X-ray diffraction analysis.

References

.
Transition metal complex-mediated chemistry of 1,3,5-cycloheptatrienes
Dyakonov V.A., Kadikova G.N., Dzhemilev U.M.
Russian Chemical Reviews, 2018
.
A Unified Entry into the Ingenane, Tigliane, and Taxane Ring Systems
Rigby J.H., Niyaz N.M., Short K., Heeg M.J.
Journal of Organic Chemistry, 1995
.
Development of ST-246® for Treatment of Poxvirus Infections
Jordan R., Leeds J.M., Tyavanagimatt S., Hruby D.E.
Viruses, 2010
.
N-(3,3a,4,4a,5,5a,6,6a-Octahydro-1,3-dioxo-4,6- ethenocycloprop[f]isoindol-2-(1H)-yl)carboxamides:  Identification of Novel Orthopoxvirus Egress Inhibitors
Bailey T.R., Rippin S.R., Opsitnick E., Burns C.J., Pevear D.C., Collett M.S., Rhodes G., Tohan S., Huggins J.W., Baker R.O., Kern E.R., Keith K.A., Dai D., Yang G., Hruby D., et. al.
Journal of Medicinal Chemistry, 2007
.
Highly Selective Cobalt-Mediated [6 + 2] Cycloaddition of Cycloheptatriene and Allenes
Clavier H., Jeune K.L., Riggi I.D., Tenaglia A., Buono G.
Organic Letters, 2010
.
Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis
Ito T., Harada S., Homma H., Takenaka H., Hirose S., Nemoto T.
Journal of the American Chemical Society, 2020
.
The Preparation of Cyclic Ketones by Ring Enlargement
Kohler E.P., Tishler M., Potter H., Thompson H.T.
Journal of the American Chemical Society, 1939
.
Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride
Ishitobi H., Tanida H., Tori K., Tsuji T.
Bulletin of the Chemical Society of Japan, 1971
.
Titanium-Catalyzed [6π+2π]-Cycloaddition of Alkynes and Allenes to 7-Substituted 1,3,5-Cycloheptatrienes
D'yakonov V.A., Kadikova G.N., Kolokol'tsev D.I., Ramazanov I.R., Dzhemilev U.M.
European Journal of Organic Chemistry, 2015
.
Dynamic Equilibria in the Products of Intramolecular Buchner Additions of Diazoketones to Aryl Rings Bearing Methoxy Substituents
Maguire A.R., O'Leary P., Harrington F., Lawrence S.E., Blake A.J.
Journal of Organic Chemistry, 2001
.
Synthesis and reactions of 1,6-dithiocyanato- and 1,6-diiodo-1,3,5-cycloheptatrienes
Okazaki R., Ooka M., Tokitoh N., Inamoto N.
Journal of Organic Chemistry, 1985
.
Tivantinib (ARQ197) Displays Cytotoxic Activity That Is Independent of Its Ability to Bind MET
Basilico C., Pennacchietti S., Vigna E., Chiriaco C., Arena S., Bardelli A., Valdembri D., Serini G., Michieli P.
Clinical Cancer Research, 2013
.
Research progress in biological activities of succinimide derivatives
Zhao Z., Yue J., Ji X., Nian M., Kang K., Qiao H., Zheng X.
Bioorganic Chemistry, 2021
.
Kaagman J.F., Rep M., Horáček M., Sedmera P., Čejka J., Varga V., Mach K.
Collection of Czechoslovak Chemical Communications, 2002