Diastereoselective Dearomatization of Chalcone‐Based Quinolinium Salts to Assemble Bridged Quinobenzazepine Polycycles DOI Open Access

Chengxiang Luo,

Chaoyang Li, Lijie Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 13, 2023

Abstract Quinobenzazepines are useful in medicinal chemistry, but their synthesis is very challenging. Herein, we designed and synthesized a range of multi‐functional chalcone‐based quinolinium salts; synthetic application the rapid straightforward construction quinobenzazepines was successfully explored. A wide oxa‐bridged quinobenzazepine polycycles were afforded serendipitously through dearomative cascade reaction our newly developed salts acetylacetone. This strategy features high bond‐ ring‐forming efficiency complete regio‐ diastereoselective control.

Language: Английский

Divergent Synthesis of Sulfur‐Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4‐Zwitterionic Thiolates and Bicyclobutanes DOI
Yuanjiu Xiao, Feng Wu, Lei Tang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: May 31, 2024

Bridged cyclobutanes and sulfur heterocycles are currently under intense investigation as building blocks for pharmaceutical drug design. Two formal cycloaddition modes involving bicyclobutanes (BCBs) pyridinium 1,4-zwitterionic thiolate derivatives were described to rapidly expand the chemical space of sulfur-containing bridged cyclobutanes. By using Ni(ClO

Language: Английский

Citations

19

Recent advances in the dearomative functionalisation of heteroarenes DOI Creative Commons
Nicolas Kratena, Bruno Marinič, Timothy J. Donohoe

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(48), P. 14213 - 14225

Published: Jan. 1, 2022

This Perspective outlines the myriad of products that can be obtained by dearomatisation and functionalization heteroarene substrates. Complex 3D molecules often prepared in one step from simple arene starting materials.

Language: Английский

Citations

55

Indole frameworks via transition-metal-free annulation: a current perspective DOI
Suven Das

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(29), P. 13729 - 13775

Published: Jan. 1, 2023

The present review summarizes recent (2019–mid-2023) efforts towards the construction of indole core via transition-metal-free methods.

Language: Английский

Citations

11

One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines DOI
Pallab Karjee, Bijoy Debnath, Santu Mandal

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(30), P. 4068 - 4071

Published: Jan. 1, 2024

A two step one-pot annulation of donor–acceptor cyclopropanes with tetrahydroisoquinolines has been accomplished to furnish benzo-fused indolizines substrate scope and functional group diversity.

Language: Английский

Citations

4

Divergent Synthesis of Sulfur‐Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4‐Zwitterionic Thiolates and Bicyclobutanes DOI
Yuanjiu Xiao, Feng Wu, Lei Tang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(40)

Published: May 31, 2024

Abstract Bridged cyclobutanes and sulfur heterocycles are currently under intense investigation as building blocks for pharmaceutical drug design. Two formal cycloaddition modes involving bicyclobutanes (BCBs) pyridinium 1,4‐zwitterionic thiolate derivatives were described to rapidly expand the chemical space of sulfur‐containing bridged cyclobutanes. By using Ni(ClO 4 ) 2 catalyst, an uncommon higher‐order (5+3) BCBs with quinolinium was achieved broad substrate scope mild reaction conditions. Furthermore, first Lewis acid‐catalyzed asymmetric polar BCB pyridazinium accomplished. In contrast, thiolates undergo Sc(OTf) 3 ‐catalyzed (3+3) generate thia‐norpinene products, which represent initial instance synthesizing 2‐thiabicyclo[3.1.1]heptanes (thia‐BCHeps) from BCBs. Moreover, we have successfully used this protocol prepare thia‐BCHeps‐substituted analogues bioactive molecule Pitofenone. Density functional theory (DFT) computations imply that kinetic factors govern between thiolate, whereas is thermodynamic control.

Language: Английский

Citations

3

Facile photocatalytic reactions in various conditions using quinolinium salts as photocatalysts DOI

Ye Han,

Sang Bong Lee

Journal of Industrial and Engineering Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

Citations

0

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions DOI Creative Commons
Zhen‐Hua Wang, Yong You, Jian‐Qiang Zhao

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(7), P. 3059 - 3059

Published: March 29, 2023

Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles have received increasing attention recent years. In particular, pyridinium quinolinium 1,4-zwitterions been widely studied used a variety cyclization reactions due to their air stability, ease use, high efficiency. Sulfur- nitrogen-based 1,4-zwitterions, types emerging heteroatom-containing synthons, attracted much from chemists. These which contain multiple reaction sites, successfully synthesis three- eight-membered cyclic compounds over last decade. this review, we present exciting progress made field sulfur- 1,4-zwitterions. Moreover, mechanistic insights, transition states, some synthetic applications, challenges opportunities also discussed. We hope provide an overview for chemists who interested heterocycle with

Language: Английский

Citations

7

(3+2) Cycloaddition of Heteroaromatic N-Ylides with Sulfenes DOI
Kosuke Yamamoto,

Kohei Torigoe,

Masami Kuriyama

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 798 - 803

Published: Jan. 22, 2024

A (3+2) cycloaddition of heteroaromatic N-ylides with sulfenes, which are generated in situ from sulfonyl chlorides, has been developed. variety ylides were transformed into the corresponding sulfone-embedded N-fused heterocycles high yields. Hexafluoroisopropyl mesylate was demonstrated to be a suitable reactant for quinolinium ylides. Furthermore, this could performed an ylide prepared by Cu-catalyzed transfer reaction one-pot manner, extending substrate scope unisolable ylide.

Language: Английский

Citations

2

Organocatalyzed Enantio- and Diastereoselective Formal Domino 1,3-Dipolar Cycloaddition/Rearrangement: Synthesis of Chiral Pyrrolo-thiazine-2-carbaldehydes DOI

Solai Pandidurai,

Venkata Surya Kumar Choutipalli,

V. Subramanian

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2971 - 2975

Published: March 28, 2024

An efficient approach for the synthesis of chiral pyrrolo[1,2-

Language: Английский

Citations

2

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules DOI
Suven Das

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(18), P. 8243 - 8276

Published: Jan. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Language: Английский

Citations

2