Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives DOI
Chunjie Ni,

Zhanhang Liang,

Xiaojuan Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16711 - 16720

Published: Oct. 31, 2024

A phosphine-catalyzed [4 + 1] annulation of β'-acetoxy allenoate with α-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization succinimides, resulting in formation functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope yields ranging from moderate to excellent under optimized conditions. In addition, biological evaluation indicates that cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, HepG2).

Language: Английский

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2762 - 2767

Published: Jan. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Language: Английский

Citations

9
Tertiary‐Amine Controlled (3+3) or (4+2) Annulations of β′‐Acetoxy Allenoates with N‐Sulfonyl Ketimines: An Entry to m‐Teraryl and Fused Dihydropyridines DOI
Asif Ali Qureshi,

A. Sanjeeva Kumar,

K. C. Kumara Swamy

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1165 - 1175

Published: Jan. 10, 2024

Abstract Lewis base dependent (3+3) and (4+2) annulations of β′ ‐acetoxy allenoates with N ‐sulfonyl ketimines offer m ‐teraryl fused dihydropyridines varying substituents depending on the tertiary amine as well subtle changes in reaction conditions. The triazabicyclodecene (TBD)‐catalyzed annulation involves 1,2‐elimination followed by 6‐ endo ‐dig cyclization key steps delivering 1,4‐hydropyridines. same reactants under DMAP catalysis via Mannich coupling, rather than C−N bond cleavage/aromatization. Key intermediates have been identified HRMS studies.

Language: Английский

Citations

4
Synthesis of tetrahydroquinoline derivatives via electrochemical hydrocyanomethylation or hydrogenation of quinolines with MeCN DOI
Jie Xia, Dahan Wang, Ruitong Yang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5160 - 5166

Published: Jan. 1, 2024

Electrochemical hydrocyanomethylation of quinoline skeletons employing acetonitrile as both a hydrogen resource and cyanomethyl precursor has been described.

Language: Английский

Citations

4
Acetoxy allenoates as emerging synthons in annulation/cycloaddition reactions DOI
K. C. Kumara Swamy, Sachin Chauhan, Sanjeeva K. Arupula

et al.

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

Published: Jan. 1, 2025

The emergence of acetoxy allenoates as versatile synthons to generate a plethora annulation/cycloaddition products via electrophilic diene–phosphonium/ammonium intermediates is highlighted in this feature article.

Language: Английский

Citations

0
Progress in Synthesis of Medium-Sized Ring Compounds Catalyzed by Organophosphine DOI

Xuling Pan,

You Huang

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3609 - 3609

Published: Jan. 1, 2024

Language: Английский

Citations

2
A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK DOI

Jingxiong Lai,

You Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(15), P. 2066 - 2069

Published: Jan. 1, 2024

A CH 3 OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.

Language: Английский

Citations

1
Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation DOI
Sachin Chauhan, K. C. Kumara Swamy

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10816 - 10830

Published: July 15, 2024

Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β'-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed gives benzothiazole-fused 1,4-dihydropyridine carboxylates (3 + 3) chemoselectively. By contrast, PR

Language: Английский

Citations

1
Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives DOI
Chunjie Ni,

Zhanhang Liang,

Xiaojuan Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5116 - 5121

Published: Jan. 1, 2024

Novel methods for constructing functionalized 1,3-diazepine and 1,4-diazocine derivatives have been disclosed through phosphine-catalyzed [4 + 3] 4] annulations of β′-acetoxy allenoates with N , -dinucleophiles.

Language: Английский

Citations

1
Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives DOI
Chunjie Ni,

Zhanhang Liang,

Xiaojuan Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16711 - 16720

Published: Oct. 31, 2024

A phosphine-catalyzed [4 + 1] annulation of β'-acetoxy allenoate with α-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization succinimides, resulting in formation functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope yields ranging from moderate to excellent under optimized conditions. In addition, biological evaluation indicates that cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, HepG2).

Language: Английский

Citations

1