Home / Publications / Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide

Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide

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, 450075 Ufa, Russian Federation
10.71267/mencom.7785
Published 2025-10-21
Communication , Volume 35, Issue 6, 723-725
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Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 723-725.
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Kadikova G. N., Meshcheryakova E. S., Khalilov L. M. Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 723-725.
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TY - JOUR
DO - 10.71267/mencom.7785
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7785
TI - Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide
T2 - Mendeleev Communications
AU - Kadikova, Gulnara Nazifovna
AU - Meshcheryakova, Ekaterina Sergeevna
AU - Khalilov, Leonard Mukhibovich
PY - 2025
DA - 2025/10/21
PB - Mendeleev Communications
SP - 723-725
IS - 6
VL - 35
ER -
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@article{2025_Kadikova,
author = {Gulnara Nazifovna Kadikova and Ekaterina Sergeevna Meshcheryakova and Leonard Mukhibovich Khalilov},
title = {Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7785},
number = {6},
pages = {723--725},
doi = {10.71267/mencom.7785}
}
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Kadikova, Gulnara Nazifovna, et al. “Access to 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide.” Mendeleev Communications, vol. 35, no. 6, Oct. 2025, pp. 723-725. https://mendcomm.colab.ws/publications/10.71267/mencom.7785.

Keywords

1,3,5-cycloheptatrienes
2,4,6-triazatetracyclo-[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones
azodicarboxylic acid N-phenylimide
biologically active compounds
hetero-Diels–Alder reaction

Abstract

Novel 2,4,6-triazatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-diones were prepared in high yields (86--96%) via the hetero-Diels–Alder reaction of azodicarboxylic acid N-phenylimide with 7-substituted cycloheptatrienes. The adducts are formed exclusively via the endo-addition of the azo dienophile to bicyclo[4.1.0]hepta-2,4-diene, the norcaradiene tautomer. The cyclopropane ring in the adduct is syn-oriented relative to the double bond and contains an exo-directed substituent.

Funders

Russian Science Foundation
24-23-00011