Chemical Papers, Journal Year: 2024, Volume and Issue: 78(10), P. 5985 - 5991
Published: May 23, 2024
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1780 - 1786
Published: Feb. 27, 2024
Herein we demonstrate a novel organocatalytic method to access multifunctionalized naphthalenes via an NHC-catalyzed reaction of ynones and o-formyl-tethered Michael acceptors. The presented proceeds through intermolecular Stetter reaction–cyclization–aromatization cascade represents rare example benzannulation for the synthesis substituted arenes by using ynone as two-carbon synthon. current has broad substrate scope; postsynthetic transformations gram-scale syntheses highlight practicality displayed methodology.
Language: Английский
Citations
6
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 5, 2025
A one-step synthetic method to access medicinally essential anthraquinones has been developed by reacting Kobayashi's aryne precursors with 3-sulfonylphthalides following [4 + 2] Hauser–Kraus annulation reaction. The implemented for the total synthesis of bioactive natural products, chrysophanol, danthron, and physcion in 30, 20, 36% overall yields, respectively, from known compounds.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 15, 2025
The Hauser-Kraus annulation of sulfonylphthalide with Morita-Baylis-Hillman (MBH) adducts nitroalkenes provides access to phenanthrenes and naphthoquinone fused dihydrobenzoxepines. H-K results in naphthoquinones bearing a key alcohol group protected form, which leads tetracyclic oxepines upon reaction formaldehyde. These alcohols yield functionalized via oxidation [3 + 3] β-ketoesters.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 11067 - 11071
Published: July 23, 2024
An unprecedented divergent aromatization reaction of α-halobenzyl γ-butenolides has been described for the selective and concise synthesis highly substituted benzo higher π-extended fluorenones, 1,3-disubstituted naphthalenes depending on migration ability quaternary α-substituent. This switch from Ag
Language: Английский
Citations
3
Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 141274 - 141274
Published: Dec. 1, 2024
Language: Английский
Citations
3
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17)
Published: Aug. 19, 2024
The Hauser-Kraus annulation is one of the most powerful methods to construct polycyclic hydroquinone from 3-cyano phthalides and Michael acceptors. Although these have been developed for more than 46 years, asymmetric catalytic version has remained underdeveloped. Inspired by N-heterocyclic carbene (NHC)-catalyzed Stetter reaction via Breslow intermediate, herein, we an NHC-catalyzed enantioselective a phthalide-type intermediate. With help NHC catalyst ynamide coupling reagent, proceeds under mild conditions at room temperature, giving corresponding chiral in moderate good yields, with high enantioselectivities. key intermediate was successfully isolated confirmed. kinetic thermal dynamic features cascade were also explored density functional theory (DFT) calculation. Learning wide application annulation, this method hopeful bring shortcuts facile synthesis sophisticated compounds. Besides, discovery expand synthetic potentials organocatalysis.
Language: Английский
Citations
2
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(41)
Published: July 31, 2024
Abstract Tf 2 NH‐mediated decarboxylative dearomatization reaction of benzonorcaradiene γ‐ketoacids, in situ generated by intramolecular alkenylation alkynylcyclopropane γ‐ketoacids or their tert ‐butyl esters, has been described for regioselective synthesis polyfunctionalized 1‐acylmethyl‐4‐arylnaphthalenes.
Language: Английский
Citations
2
Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: unknown
Published: Nov. 10, 2023
The Hauser-Kraus (H-K) annulation of N-unsubstituted 3-olefinic oxindoles with 3-nucleophilic phthalides triggers a cascade ring expansion and contraction reactions through several regioselective steps in one pot. While oxazepines were isolated the presence stoichiometric amounts base at room temperature, carbazoles phenanthridinediones products excess microwave irradiation. Mechanistic studies guided by stepwise control experiments revealed that isolable oxazepine intermediate, formed via H-K adduct, is key precursor to carbazole phenanthridinedione decarboxylative cyclizations.
Language: Английский
Citations
1
Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown
Published: Feb. 28, 2024
Abstract We have achieved an efficient synthesis of C(3)-arylphthalides by coupling C(3)-bromophthalides and arylboronic acids under palladium catalysis. The C(sp 3 )-C(sp 2 ) worked well in the presence water to provide products a high yield.
Language: Английский
Citations
0
Chemical Papers, Journal Year: 2024, Volume and Issue: 78(10), P. 5985 - 5991
Published: May 23, 2024
Language: Английский
Citations
0