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

External photocatalyst-free C-H alkylation of N-sulfonyl ketimines with alkanes under visible light DOI

Hai‐Yang Song,

Fang Xiao,

Jun Jiang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(9), P. 108509 - 108509

Published: April 28, 2023

Language: Английский

Citations

53

Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines DOI

Anzai Shi,

Kai Sun, Xiaolan Chen

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 299 - 303

Published: Dec. 16, 2021

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst can be simply recovered from mixture reused at least five times without an obvious reduction in its reactivity, exhibiting high economic feature.

Language: Английский

Citations

58

Solvent-Controlled Silver Catalyzed Radical Transformation of α-Imino-Oxy Acids with Cyclic Aldimines DOI
Jingjing Wang, Yong Qin,

Ke Cui

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A silver-catalyzed cross coupling of cyclic aldimines and α-imino-oxy acids has been developed. The solvent-dependent reaction could selectively deliver either imine moiety retained nitriles or ring-opened oxonitriles in moderate yields.

Language: Английский

Citations

1

Electrochemically driven oxidative C–H/N–H cross-coupling reactions of cyclic sulfamidate imines with primary anilines and secondary amines DOI
Haixia Wang,

Zhi-Hao Li,

Wanwan Li

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(21), P. 8377 - 8385

Published: Jan. 1, 2022

An efficient and eco-friendly electrochemical synthesis of various cyclic N -sulfonylamidines from sulfamidate imines amines via oxidative C–H/N–H cross-coupling under mild reaction conditions has been developed.

Language: Английский

Citations

18

Visible-light-induced cyclization of cyclic N-sulfonyl ketimines to N-sulfonamide fused imidazolidines DOI
Xiaotong Wang,

Anzai Shi,

Xianqiang Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(18), P. 3798 - 3802

Published: Jan. 1, 2022

A visible-light-induced metal-free cascade cyclization of cyclic N-sulfonyl ketimines with N-arylglycines for the construction N-sulfonamide-fused imidazolidines was developed. The procedure employed 3 mol% eosin Y as photocatalyst at room temperature under visible light irradiation, providing various in good yields (32 examples, up to 86% yields).

Language: Английский

Citations

17

PhI(OAc)2/I2‐Mediated Decarboxylative C4‐Amination of Coumarin‐3‐Carboxylic Acids via Csp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions DOI
Anindita Bhowmick, Goutam Brahmachari

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(15)

Published: March 6, 2023

Abstract An efficient and straightforward protocol for accessing a new series of functionalized 4‐aminocoumarins from PIDA/I 2 ‐mediated decarboxylative C 4 ‐amination coumarin‐3‐carboxylic acids via direct sp2 −H dehydrogenative C−N cross‐coupling with secondary amines under ambient conditions has been accomplished. The notable advantages this are the tolerance diverse functional groups, mild reaction at temperature, moderate to good yields, short times (in minutes), high regioselectivity, gram‐scale applicability, eco‐friendliness. This is first report cross‐dehydrogenative coupling synthesizing 4‐aminocoumarins.

Language: Английский

Citations

5

Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives DOI
Kai Liu, Feng Li, Jingjing Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2700 - 2704

Published: Jan. 1, 2023

A silver-catalyzed cyclization of α-imino-oxy acids under mild conditions has been described. This reaction offers facile access to a diverse range fused tetralone derivatives with exquisite stereoselectivity in moderate good yields.

Language: Английский

Citations

4

Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines DOI Creative Commons
Jingjing Wang, Feng Li, Kai Liu

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 1, 2023

We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. mechanistic study revealed radical process. In addition, the usefulness organic synthesis was proved by scale-up as well late-stage modification drug-like molecules.

Language: Английский

Citations

4

CeCl3-Catalyzed C–H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer DOI
Bin Zhou, Min Dong, Wei Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(24), P. 18337 - 18343

Published: Dec. 9, 2024

A cerium-catalyzed C–H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical an HAT reagent air green oxidant. series alkylated were synthesized moderate to good yields in highly atom-economic manner under chemical oxidant-free conditions.

Language: Английский

Citations

1

Catalyst‐Free, Air‐Mediated C(sp2)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids DOI
Jie Zhang, Xiaolan Li,

Lieqiang Liao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4544 - 4549

Published: Nov. 22, 2023

Abstract The air mediated radical alkylation of cyclic aldimines via autoxidation alkylboronic acids has been realized under mild reaction conditions. By simply heating with acid using as sole oxidant, this protocol provides a catalyst‐free access to variety alkylated 21–91% yields. Preliminary mechanistic studies suggest that pathway might be involved in the reaction.

Language: Английский

Citations

3