Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 251 - 280
Published: Jan. 1, 2023
Language: Английский
Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: May 26, 2025
Abstract A dearomatization reaction between electron‐deficient indoles and α,α‐diaryl‐substituted methyleneisocyanides, followed by in situ Friedel–Crafts alkylation, is described. In a telescoped mediated Brønsted base the first step acid second step, aryl‐substituted pyrrolo[3,4‐b]indole cores are generally obtained moderate‐to‐good yields with high diastereoselectivity. The tolerates wide range of 3‐nitroindoles aryl nucleophiles; however, substrate scope isocyanide derivatives limited. developed methodology offers modular approach for synthesis multi‐substituted polycyclic cores.
Language: Английский
Citations
0
Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 1163 - 1163
Published: March 5, 2024
An efficient dearomative (3 + 2) cycloaddition of para-quinamines and 2-nitrobenzofurans has been developed. This reaction proceeds smoothly under mild conditions affords a series benzofuro[3,2-b]indol-3-one derivatives in good to excellent yields (up 98%) with perfect diastereoselectivities (all cases > 20:1 dr). The scale-up synthesis versatile derivatizations demonstrate the potential synthetic application protocol. A plausible mechanism is also proposed account for observed process. work represents first instance N-triggered 2-nitrobenzofurans.
Language: Английский
Citations
3
Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3630 - 3650
Published: Oct. 3, 2022
Abstract Electron‐withdrawing groups (EWG) have emerged as a powerful tool for the activation of various arenes to promote nucleophilic dearomative additions construction complicated chiral cyclic structures under asymmetric catalytic systems. Nitro‐indoles, nitro‐benzofurans/benzothiophenes, and related nitro‐heteroarenes are widely applied in reaction with nucleophiles construct enantioenriched polycyclic skeletons via dearomatization process. Meanwhile, electron‐deficient azo‐group nitroso‐group an alternative arenes, which enable formal aromatic arylations electrophilic aromatics novel biaryl atropisomers. Besides, azo‐naphthanenes served dipolar surrogates dipolarophiles proceed cycloadditions skeletons. The EWG‐tethered arene has proven be versatile protocol structurally diversified backbones. This review summarizes latest progress involved transformations organo‐ or transition metal catalysis. magnified image
Language: Английский
Citations
11
Organic Letters, Journal Year: 2023, Volume and Issue: 25(30), P. 5608 - 5612
Published: July 24, 2023
A novel procedure for the synthesis of α,α-diaryl-α-amino acid derivatives has been developed. Silver oxide catalyzes conjugate addition α-aryl isocyanoacetates to o-quinone diimide, affording corresponding α,α-diarylisocyano esters in excellent yields and regioselectivities short reaction times. Acid hydrolysis isocyano group provides amino acids bearing a diarylated tetrasubstituted carbon atom. The is also amenable α-alkyl-α-arylisocyano esters, while with 3-hydroxy diimides 4H-benzo[e][1,3]oxazines via addition/cyclization process.
Language: Английский
Citations
6
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 10810 - 10817
Published: July 18, 2023
The synthesis of 3-thioether-substituted dihydrofuro[2,3-b]benzofurans involving the [3 + 2] coupling sulfur ylides with 2-nitrobenzofurans has been realized in moderate to good yields under mild conditions without any precious catalysts or additives. It is worth mentioning that reutilization departed nitro-anion reaction process facilitates this new chemical transformation and presents a manner high atom economy provide products complex structure.
Language: Английский
Citations
4
ACS Omega, Journal Year: 2023, Volume and Issue: 8(7), P. 6854 - 6859
Published: Feb. 9, 2023
Herein, we report that under mild and transition-metal-free conditions an unprecedented practical SN2' reaction of Morita-Baylis-Hillman adducts with isocyanoacetates takes place in a stereo- regiospecific manner. This which tolerates wide variety functionalities delivers transformable α-allylated high efficiencies. Preliminary studies on the asymmetric version this indicate ZnEt2/chiral amino alcohol combinations are catalytic system for transformation, giving enantioenriched isocyanoacetate chiral quaternary carbon yield.
Language: Английский
Citations
2
Chemistry of Heterocyclic Compounds, Journal Year: 2023, Volume and Issue: 59(4-5), P. 183 - 192
Published: May 1, 2023
Language: Английский
Citations
1
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(24)
Published: April 26, 2024
Abstract The first palladium‐catalyzed allylation of isocyanoacetates with vinyl aziridines has been developed. reaction conditions were suitable for a variety α‐aryl as well N ‐substituted aziridines, affording the corresponding products in moderate to high yields (up 98 %) along excellent stereoselectivity and regioselectivity. Transformations into trans ‐4,5‐dehydrolysine analogues highly functionalized proline ester derivative further demonstrated, preliminary asymmetric version also evaluated.
Language: Английский
Citations
0
Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 251 - 280
Published: Jan. 1, 2023
Language: Английский
Citations
0