Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe DOI Creative Commons

Michael Fragkiadakis,

Eirini Fotopoulou, Konstantinos G. Froudas

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 31, 2024

Abstract Cyclic N ‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities these four different isocyanide‐based multicomponent reactions. Our goal was to create libraries compounds functional groups vectors that are compatible for structural elaboration optimization their physical properties. We synthesized 15 unprecedented high diversity complexity, whereas have obtained single crystal structures each scaffold, unraveling geometrical features potential employment drug discovery.

Language: Английский

Base-Promoted and Copper(I)-Catalyzed Tandem Cyclization-C(sp2)-N Coupling of Vinyl Malononitriles with Ortho-Nitrochalcones: Access to Acridones and their Fused Derivatives DOI

Raju Lal Dhakar,

S Banuprakash Goud,

Sampak Samanta

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

An efficient Cs2CO3-promoted and copper(I)-catalyzed double cyclization of ortho-nitrochalcones with vinyl malononitriles for the de novo access to a variety tri- tetra-substituted acridones their fused derivatives value-added CN group has been developed first time. This one-pot operation proceeds through Michael-cyclization-aromatization, followed by regioselective ipso-amination via nucleophilic aromatic substitution (SNAr) reaction, resulting in two C═C bonds C-N bond acridone ring synthesis. economic strategy based on 100% carbon atoms ensures successive formation rings operation, good high yields, wide range substrates, tolerance functionalities. In addition, were converted into several acridines, highlighting synthetic versatility usefulness prepared derivatives.

Language: Английский

Citations

0
A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides DOI
Shuting Zhang,

Wen Gu,

Fei Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Organic selenium compounds are important molecules with a wide range of applications in pharmaceuticals, organic materials, catalysis, and other fields. Herein, we report the synthesis α-selenomethylketones through reaction vinyl azides arylselenols benzylselenol. This protocol has advantages releasing only nitrogen as benign byproduct, using air an environmentally friendly initiator, very short duration, mild conditions, broad substrate compatibility. The results exploratory studies show that oxygen is used initiator to promote this radical cascade reaction.

Language: Английский

Citations

0
Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art DOI
Lucas G. Furniel, Arlene G. Corrêa

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(9)

Published: May 13, 2024

Abstract The development of greener methods for the preparation three‐membered rings has increased in last decade, not only due to their biological activity but also ring strain those heterocycles that make them useful precursors more complex molecules. In this work, visible‐light‐promoted synthesis and ring‐opening aziridines epoxides, reported five years, were reviewed. Both homogeneous heterogeneous catalysts discussed and, addition, plausible mechanism pathways highlighted.

Language: Английский

Citations

1
Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe DOI Creative Commons

Michael Fragkiadakis,

Eirini Fotopoulou, Konstantinos G. Froudas

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 31, 2024

Abstract Cyclic N ‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities these four different isocyanide‐based multicomponent reactions. Our goal was to create libraries compounds functional groups vectors that are compatible for structural elaboration optimization their physical properties. We synthesized 15 unprecedented high diversity complexity, whereas have obtained single crystal structures each scaffold, unraveling geometrical features potential employment drug discovery.

Language: Английский

Citations

0