Communications

Access to 2,4,6-triazatetracyclo[5.3.2.0^2,6.0^8,10]dodecenes by the hetero-Diels–Alder reaction between cycloheptatrienes and azodicarboxylic acid imide

G. N. Kadikova, E. S. Meshcheryakova, L. M. Khalilov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, 450075 Ufa, Russian Federation

Аннотация: Novel 2,4,6-triazatetracyclo[5.3.2.0^2,6.0^8,10]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.

Ключевые слова: hetero-Diels–Alder reaction, 1,3,5-cycloheptatrienes, azodicarboxylic acid N-phenylimide, 2,4,6-triazatetracyclo-[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-diones, biologically active compounds.

Поступила в редакцию: 01.04.2025
Принята в печать: 27.05.2025

Язык публикации: английский

DOI: 10.71267/mencom.7785

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