Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?

Journal of Organic Chemistry. 2023. Vol. 88. No. 19. P. 13782–13795.

Yaremenko I., Belyakova Y., Radulov P., Michael G. Medvedev, Krivoshchapov N., Alabugin I., Terent’ev A.

Relief of stereoelectronic frustration drives the acid-catalyzed three-component condensation of β,δ′-triketones with hydrazides and H2O2 to the direction where both nucleophiles and all three electrophilic carbons are involved in the formation of a tricyclic sp3-rich ring system that includes four heteroatoms. The otherwise inaccessible tricyclic N-substituted aminoperoxides are prepared rapidly and selectively from relatively simple substrates in good to high yields.

Ключевые слова: atomistic modeling, quantum chemistry, квантовая химия, Атомистическое и многомасштабное моделирование

ПУБЛИКАЦИЯ ПОДГОТОВЛЕНА ПО РЕЗУЛЬТАТАМ ПРОЕКТА: Разработка функционалов ТФП и применение методов квантовой химии для нужд практической химии (2023)