Synthesis of 2-amidoindenone derivatives through an ynamide carbosilylation/Houben–Hoesch cyclization 2-step sequence DOI

Pierre Hansjacob,

Célia Schwoerer,

Frédéric R. Leroux

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 70 - 73

Published: Nov. 29, 2023

Herein we report the efficient and selective two-step synthesis of various 3-silyl-2-amidoindenones from easily accessible ynamides. This sequence involves a regio- stereo-selective silylcyanation followed by Houben-Hoesch type cyclization. Thanks to post-transformations, 3-substituted 2-amidoindenones could be obtained.

Language: Английский

Regioselective Difunctionalization and Annulation of Ynamide DOI
Shubham Dutta, Rajendra K. Mallick, Akhila K. Sahoo

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(30)

Published: April 8, 2023

Abstract The use of ynamides in organic synthesis has gained significant attention due to their ability provide access complex molecular structures through transformations such as 1,2‐difunctionalization and annulation reactions. These reactions enable the formation highly functionalized N‐bearing olefins unusual heterocycles. In this minireview, we present a systematic overview regioselective difunctionalization ynamides. We discuss multi‐component reactions, radical‐triggered functionalizations across carbon–carbon multiple bonds bifunctional reagents ynamides, highlighting potential expanding substrate scope. Furthermore, insights into mechanistic breakthroughs that have been achieved recent years development these Finally, emphasize promising future prospects versatile building blocks for architectures.

Language: Английский

Citations

28
Photoredox Radical Cascade Cyclization of 2‐Alkynylarylnitriles in Visible Light: Direct Access to 3‐Amino‐1‐indenones DOI

Shruti Rajput,

Dikshita Garg,

Nidhi Jain

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2072 - 2078

Published: March 1, 2024

Abstract A photoinduced direct synthesis of 3‐amino‐1‐indenones via radical cascade cyclization strategy is demonstrated. The methodology involves a domino reaction between 2‐alkynylarylnitrile and N ‐aminopyridinium salt captures the reactivity in‐situ generated nitrogen‐centered (NCR) in visible light. Multiple bond‐forming events including C−N, C−C, C−O take place sequentially on enabling construction 3‐amino‐1‐indenone core at room temperature 35–76% yield. preliminary biological screening synthesized compounds indicative their potent anti‐cancer property.

Language: Английский

Citations

3
Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles DOI Creative Commons
Lukáš Janecký, Petr Beier

RSC Advances, Journal Year: 2024, Volume and Issue: 14(19), P. 13640 - 13645

Published: Jan. 1, 2024

2- N -Substituted indenones, cyclopentenones or 4-carbonyl oxazoles are prepared from 5-acylated -fluoroalkyl substituted 1,2,3-triazoles and Lewis acids.

Language: Английский

Citations

2
3‐Amido‐benzo[b]silines: Straightforward Modular 2‐Step Synthesis and Photophysical Properties DOI Creative Commons

Stéphane Golling,

Tianhong Yan,

Valérie Mazan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2324 - 2333

Published: April 3, 2024

Abstract In this manuscript we report the synthesis of 3‐amido‐benzo[ b ]silines thanks to a 2‐step strategy involving 3‐component silylformylation ynamides followed by Friedel‐Crafts cyclization/isomerizing dehydration domino sequence. This reaction is tolerant various structural variations and has allowed us synthesize library diversely substituted silacycles with yields from 33 85%. We also studied fluorescence properties these compounds which show similarities recognized probes such as Si‐Rhodamine for example.

Language: Английский

Citations

1
Zinc‐Catalyzed Hydrocyanation of Ynamides and Photoisomerization, a General and Selective Access to E and Z Trisubstituted α‐Enamidonitriles DOI Creative Commons

Pierre Hansjacob,

Frédéric R. Leroux, Morgan Donnard

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(30)

Published: Feb. 27, 2023

The fully regio- and stereoselective Zn-catalyzed hydrocyanation of ynamides is reported represents a general access to various trisubstituted E-α-enamidonitriles. catalyst-free photoisomerization selectively yields the energetically comparable Z-stereoisomer. Finally, synthetic potential these new α-enamidonitriles was evaluated through synthesis original heterocycles.

Language: Английский

Citations

3
Regioselective Difunctionalization and Annulation of Ynamide DOI
Shubham Dutta, Rajendra K. Mallick, Akhila K. Sahoo

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(30)

Published: April 8, 2023

Abstract The use of ynamides in organic synthesis has gained significant attention due to their ability provide access complex molecular structures through transformations such as 1,2‐difunctionalization and annulation reactions. These reactions enable the formation highly functionalized N‐bearing olefins unusual heterocycles. In this minireview, we present a systematic overview regioselective difunctionalization ynamides. We discuss multi‐component reactions, radical‐triggered functionalizations across carbon–carbon multiple bonds bifunctional reagents ynamides, highlighting potential expanding substrate scope. Furthermore, insights into mechanistic breakthroughs that have been achieved recent years development these Finally, emphasize promising future prospects versatile building blocks for architectures.

Language: Английский

Citations

2
Synthesis of 2-amidoindenone derivatives through an ynamide carbosilylation/Houben–Hoesch cyclization 2-step sequence DOI

Pierre Hansjacob,

Célia Schwoerer,

Frédéric R. Leroux

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 70 - 73

Published: Nov. 29, 2023

Herein we report the efficient and selective two-step synthesis of various 3-silyl-2-amidoindenones from easily accessible ynamides. This sequence involves a regio- stereo-selective silylcyanation followed by Houben-Hoesch type cyclization. Thanks to post-transformations, 3-substituted 2-amidoindenones could be obtained.

Language: Английский

Citations

2