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?

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? Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2023, Volume: 88, Number: 19, Pages: 13782–13795 Pages count : DOI: 10.1021/acs.joc.3c01415

Authors

Yaremenko Ivan A. ¹ , Belyakova Yulia Yu. ¹ , Radulov Peter S. ¹ , Medvedev Michael G. ^2,1 , Krivoshchapov Nikolai V. ¹ , Alabugin Igor V. ³ , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2	HSE University, Myasnitskaya Street 20, Moscow 101000, Russian Federation
3	Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States

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.

Yaremenko I.A. , Belyakova Y.Y. , Radulov P.S. , Medvedev M.G. , Krivoshchapov N.V. , Alabugin I.V. , Terent’ev A.O.
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. V.88. N19. P.13782–13795. DOI: 10.1021/acs.joc.3c01415 WOS Scopus OpenAlex

Web of science:	WOS:001068671200001
Scopus:	2-s2.0-85174306250
OpenAlex:	W4386865028

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