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

(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

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry DOI

Archana Vijayakumar,

M. Manod,

Raveendran Bharath Krishna

et al.

RSC Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 14(12), P. 2509 - 2534

Published: Jan. 1, 2023

This review will be an essential toolbox for medicinal and bioorganic chemists seeking novel multifunctional hybrid bioactive N-heterocycles drug discovery. The work highlights the need relevance of unexplored bioisosterism employing isoquinoline-based small-molecules in design.

Language: Английский

Citations

6

Metal‐Free Electrochemical [3+2] Cycloaddition between α‐Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles DOI

Samrat Mallick,

Mrinmay Baidya, Suman De Sarkar

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(2), P. 241 - 247

Published: Nov. 24, 2023

Abstract The established strategy unveils a metal and mediator‐free electrochemical [3+2] cycloaddition approach among α ‐amino carbonyls tosylmethyl isocyanide (TosMIC) fabricating substituted imidazole scaffolds. Implementation of electro‐redox conditions on this eliminates the essential requirement transition catalysts chemical oxidants. A wide variety different functionalities are well tolerated under reaction condition, contributing to substrate scope applicability. Several control experiments cyclic voltammetry studies suggest an electro‐oxidation triggered successive C−C C−N bond formations followed by rapid aromatization for constructing five‐membered core structure.

Language: Английский

Citations

6

Rhodium-catalyzed annulation for the construction of indole core: An update DOI
Suven Das, Arpita Dutta

Tetrahedron, Journal Year: 2023, Volume and Issue: 146, P. 133633 - 133633

Published: Sept. 11, 2023

Language: Английский

Citations

4

Tandem Isomerization/α,β-Site-Selective and Enantioselective Addition Reactions of N-(3-Butynoyl)-3,5-dimethylpyrazole Induced by Chiral π–Cu(II) Catalysts DOI Creative Commons
Weiwei Guo,

Masahiro Hori,

Yoshihiro Ogura

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(49), P. 27080 - 27088

Published: Nov. 30, 2023

Allenes are important building blocks, and derivatization of products via cycloadditions allenes could become a powerful strategy for constructing carbocyclic heterocyclic rings. However, the development catalytic site-selective enantioselective cycloaddition reactions still presents significant challenges. Here, we report chiral π-Cu(II)-complex-catalyzed isomerization

Language: Английский

Citations

4

Chiral π–Cu(ii)-catalyzed site-, exo/endo-, and enantioselective dearomative (3 + 2) cycloadditions of isoquinolinium ylides with enamides, dienamides, and a trienamide DOI Creative Commons
Weiwei Guo, Jianhao Huang, Kazuaki Ishihara

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(28), P. 10926 - 10934

Published: Jan. 1, 2024

We report a dearomative (3 + 2) cycloaddition between isoquinolinium ylides and enamides, dienamides, or trienamide, which is catalyzed by chiral π–Cu( ii ) complex proceeds in site-selective, exo / endo -selective, enantioselective manner.

Language: Английский

Citations

1

Synthesis of Hexahydropyrrolo-isoquinolines by 1,3-Dipolar cycloaddition of tetrahydroisoquinolines and cinnamaldehydes DOI
You-Gui Li, Weike Chen,

You-Qiang Guo

et al.

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 122, P. 154519 - 154519

Published: April 25, 2023

Language: Английский

Citations

2

Rh(III)-Catalyzed Reaction of 4-Diazoisochroman-3-imines with (2-Formylaryl)boronic Acids To Access a Straightforward Construction of 5H-Isochromeno[3,4-c]isoquinolines DOI
Yingxiao Wang, Ming‐Hui Qi, Ping Lü

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 13544 - 13552

Published: Sept. 12, 2023

An Rh(III)-catalyzed one-pot synthesis of 5H-isochromeno[3,4-c]isoquinolines from readily available 4-diazoisochroman-3-imines and (2-formylphenyl)boronic acids is reported. The cascade annulation involves a cross-coupling an intramolecular nucleophilic addition–elimination process. A series biologically important were obtained in good to excellent yields. method can be extended synthesize 7H-isochromeno[3,4-b]thieno[3,2-d]pyridines 7H-isochromeno[3,4-b]thieno[2,3-d]pyridines the corresponding heteroaryl boronic acids.

Language: Английский

Citations

2

Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications DOI Open Access
Елена К. Белоглазкина

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(24), P. 17584 - 17584

Published: Dec. 18, 2023

Dear Colleagues, [...].

Language: Английский

Citations

1