Communications

Tracking the reactivity of arylideneimidazol-4-ones in the Diels–Alder cycloaddition

A. M. Al Mufti^ab, V. А. Ikonnikova^a, A. Yu. Smirnov^ac, P. N. Solyev^d, A. A. Korlyukov^ce, M. N. Azmi^f, M. S. Baranov^ac, A. A. Mikhaylov<sup>ac

a</sup> M. M. Shemyakin–Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russian Federation
^b D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation
^c N. I. Pirogov Russian National Research Medical University, 117997 Moscow, Russian Federation
^d V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russian Federation
^e A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119334 Moscow, Russian Federation
^f School of Chemical Sciences, University Sains Malaysia, Minden, Penang, 11800 Malaysia

Аннотация: Previously unknown [4+2]-cycloaddition of 5-arylideneimidazol-4-ones with dienes leading to 1,3-diazaspiro[4.5]deca-1,7-dien-4-ones is proceeding under either Lewis acid catalysis or upon thermal initiation. Arylideneimidazol-4-ones with electron-donating groups display low reactivity, which could be overcome by introduction of trifluoromethyl group in the 2-position of imidazol-4-one.

Ключевые слова: [4+2]-cycloaddition, Diels–Alder reaction, spirocyclic compounds, catalysis, imidazol-4-one.

Поступила в редакцию: 31.03.2025
Принята в печать: 24.04.2025

Язык публикации: английский

DOI: 10.71267/mencom.7781

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