Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 25, 2024
An I 2 -promoted oxidative annulation of three different amines enables the assembly nonsymmetrical 2,2′-biquinolines and related bis-azines through a [4π + 2σ] reaction.
Language: Английский
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1348 - 1355
Published: Jan. 13, 2024
Abstract A total synthesis strategy was developed for the of luotonin A, B and their analogues using synergistic FeCl 3 /KI‐catalyzed oxidative cyclization. This protocol utilizes cheap widely available N ‐propargyl 2‐methyl‐quinazolinones arylamines under mild conditions, it has a wide substrate scope high atom economy. Different natural products (luotonin derivatives) can be synthesized via unique switchable approach. Further transformations from to E structural modification demonstrate potential applications this method. Moreover, camptothecin also modified with reported afford hydroxyl‐substituted product.
Language: Английский
Citations
4
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(6), P. 2459 - 2471
Published: Jan. 31, 2025
A TBN-enabled tandem C-H bond oxidation/C-N cleavage/[3+2] cycloaddition of 1-nitromethyltetrahydroisoquinolines was realized, constructing a series multifunctionalized isoxazole and isoxazoline skeletons in the presence alkynes alkenes, respectively. Various functional groups were smoothly tolerated, mechanistic study revealed that construction rings is mediated by situ generated nitrile oxides.
Language: Английский
Citations
0
Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(5)
Published: Jan. 19, 2023
A series of furoxan derivatives with N-nitroso groups were synthesized in good yields by TBN initiated radical sp3 C-N bond cleavage 1-nitromethyl-N-aryltetrahydroisoquinolines. This reaction grafts the biologically important skeleton and group into on molecule, greatly improving molecular complexity one step transformation. The mechanistic study shows that this is mediated situ generated α-carbonyl nitrile oxide, which afforded promoted cleavage.
Language: Английский
Citations
4
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7330 - 7338
Published: April 29, 2024
An unprecedented protocol for the synthesis of 1,2,4-oxadiazoles from carbamates has been developed by employing nitriles as both substrates and solvents. This one-pot procedure achieves formation C═N bonds via TFA-mediated [3+2] annulation. A series are synthesized in moderate to good yields.
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(18), P. 12460 - 12469
Published: Sept. 6, 2022
A high efficiency protocol was developed for the synthesis of 2,5-disubstituted oxazoles via iodine-promoted oxidative domino cyclization. These reactions were performed with readily available methyl azaarenes and α-amino ketones under metal-free conditions. This is a simple method functional group compatibility, wide range substrates, excellent yield, providing new way to synthesize azaarene-attached oxazoles.
Language: Английский
Citations
6
ACS Omega, Journal Year: 2022, Volume and Issue: 7(42), P. 38084 - 38093
Published: Oct. 10, 2022
A highly chemoselective reaction between α,β-unsaturated trifluoromethyl ketones with azaarenes under metal-free conditions was carried out, affording a range of valuable azaarene-equipped CF3-tertiary alcohols in moderate to excellent yields (up 95% yield) good tolerance functional groups, and their structures were confirmed by NMR, HRMS, X-ray diffraction for validation. This method features simple (only solvent), high atom- step-economy, broad substrate scope. Moreover, most the target products exhibited promising fungicidal activities, compound 3al 91.65% activity against R. solani, an EC50 value 0.18 mg/mL.
Language: Английский
Citations
5
Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2787 - 2787
Published: March 20, 2023
A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse alkaloids and their derivatives via intramolecular cycloaddition methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as radical initiator source N-O. Moreover, protocol forms new C-N, C-C, C-O bonds sequence nitration annulation in a one-pot process broad substrate scope functionalization natural products.
Language: Английский
Citations
2
European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(46)
Published: Nov. 2, 2022
Abstract Treatment of CH‐diazomethane sulfonamides with tert ‐butyl nitrite produces novel sulfamoyl cyanide N ‐oxides which dimerize to form furoxanes. When the reaction is performed in presence a dipolarophile, an olefin or alkyne, dipolar cycloaddition takes place deliver isoxazolines isoxazoles, respectively.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 12, 2024
Although the transition-metal-catalyzed [3+2] cycloadditions to access isoxazoles have been described well, organocatalytic methods remain underdeveloped. Herein, we report use of an organophosphine catalyst for preparation a series with exceptional regioselectivity via cycloaddition
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 25, 2024
An I 2 -promoted oxidative annulation of three different amines enables the assembly nonsymmetrical 2,2′-biquinolines and related bis-azines through a [4π + 2σ] reaction.
Language: Английский
Citations
0