Cascade Cyclization/Annulation of β-Enamino Diketones and o-Phenylenediamine: A Strategy to Access Pyrrole-fused 1,5-Benzodiazepines DOI Creative Commons
Julia Poletto,

Julia C. M. Willig,

Jeniffer Nascimento Ascencio Camargo

et al.

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

Published: Nov. 13, 2024

Herein, we introduce an unprecedented cascade reaction for the assembly of pyrrole-fused 1,5-benzodiazepine frameworks. These diverse privileged scaffolds were controllably constructed by intramolecular cyclization β-enamino diketone, followed annulation with o-phenylenediamine. The protocol features efficient one-pot cyclization/annulation, performed under simple and mild conditions. products are obtained in a metal-free manner, good to excellent yields (65–91%), represent fused heterocyclic scaffold that is not yet found nature.

Language: Английский

Synthesis of Indole-Fused Benzodiazepine Derivatives by Photocatalyzed Cascade Reaction DOI
Tatsushi Oishi, Tatsuhiro Uchikura, Takahiko Akiyama

et al.

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

Published: Jan. 1, 2025

We report a cascade synthesis of indole-fused benzodiazepines by the photocatalyzed addition phenacyl radical, generated from α-acetoxy acetophenone, to 2-(3-methyl-1H-indol-1-yl)aniline, and subsequent cyclodehydration. A range were obtained readily available substrates.

Language: Английский

Citations

0
Photochemical aerobic sulfonylation–cyclization–selenylation to indole-fused medium-sized N-heterocycles in 2-Me-THF DOI

Tongtong Shi,

Miao Tian,

Zongfei Sun

et al.

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

Published: Jan. 1, 2025

We report a novel visible-light-induced sulfonylation cyclization and aerobic selenylation reaction for the rapid construction of highly functionalized indole-fused medium-sized diazepinones with biomass feedstock 2-Me-THF as medium.

Language: Английский

Citations

0
Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones DOI
Shutao Wang, W. Y. Zhang,

Zhuoqi Zhang

et al.

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

Published: April 11, 2025

A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita-Baylis-Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a N-allylic alkylation of the indole scaffold with MBH carbonates, followed intramolecular Michael cyclization. Notably, selectivity this process controlled removable o-methoxyphenyl (OMP) directing group attached indole-2-carboxamides. The wide scope substrates, high regio- stereoselectivity, diverse transformations highlight potential synthetic utility method in drug discovery.

Language: Английский

Citations

0
Visible-Light-Induced Sulfonylation Cyclization to Generate Indole-Fused Medium-Sized N-Heterocycles in 2-Me-THF DOI

Tongtong Shi,

Miao Tian, Yanping Zhu

et al.

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

Published: Feb. 27, 2025

A novel visible-light-induced sulfonylation cyclization to indole-fused medium-sized N-heterocycles was established under room temperature with biomass-derived 2-Me-THF as the solvent. This reaction proceeds in absence of external photocatalyst, additive, metal salts, and base. Broad substrate scope, good functional group compatibility, large-scale synthesis derivatization via iodination, nitration, chlorination, cyanation, selenylation demonstrate utility this protocol. radical route proposed based on inhibition experiments, visible-light irradiation on-off test, apparent quantum efficiency calculation, UV-vis absorption spectroscopic studies.

Language: Английский

Citations

0
Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters DOI
Zhi Zhang,

Miao-Miao Ji,

Xiao‐Feng Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9001 - 9010

Published: June 6, 2024

2,3-Allenamides are an important class of unsaturated group-substituted carbonyl compounds. A palladium-catalyzed aminocarbonylation propargyl acetates with amines for the synthesized tri-/tetrasubstituted 2,3-allenamides has been developed. broad range have prepared from in good to excellent yields. The reaction featured mild conditions and functional group tolerance. applicability this methodology was further highlighted by late-stage modification several natural products pharmaceuticals.

Language: Английский

Citations

1
Synthesis of 1,2'‐Spirobi[indene]‐1,3‐diones by Pd(II)‐Catalyzed C‐H Activation and Alkynes Annulation Reaction DOI
Xuefeng Xu,

Lintao Yu,

Mengfan Chang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2926 - 2932

Published: May 15, 2024

Abstract An intermolecular annulation reaction of 2‐aryl‐1,3‐indandions with alkynes was reported using Pd(OAc) 2 to access spirobi[indene]‐1,3‐diones. Under palladium catalysis, the substrates form a homocoupling dimer intermediate through catalytic dehydrogenative cross‐coupling process. The palladium(II) species could come from or 2‐aryl‐1,3‐indandion. Notably, this pathway is not typically observed in enol‐directed formal sp 3 C−H functionalization/oxidative chemistry. This transformation provides route class functionalized spiro carbocyclic indenes.

Language: Английский

Citations

0
Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐heterocycles with N‐methoxyindoleamides and Isoxazolones DOI

Dan‐Ting Shen,

Wen‐Xuan Zou,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4089 - 4094

Published: July 20, 2024

Abstract A method for synthesizing pyrimido[ 1,2‐a ]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C−H activation/annulation strategy employing N ‐methoxyindoleamides and isoxazolones is developed. Also, framework of 3‐methoxy‐2,3‐dihydro‐[ 1,3,5 ]triazino[ ]indole‐4,10‐dione was successfully synthesized Cp*Rh‐catalyzed activation/annulation/oxidation reaction between N‐ (methyloxy)‐1 H ‐indole‐1‐carboxamide isoxazolones. These reactions demonstrated the suitability several substrates, compatibility with numerous functional groups, mild conditions. Preliminary mechanistic investigations have been completed.

Language: Английский

Citations

0
Cascade Cyclization/Annulation of β-Enamino Diketones and o-Phenylenediamine: A Strategy to Access Pyrrole-fused 1,5-Benzodiazepines DOI Creative Commons
Julia Poletto,

Julia C. M. Willig,

Jeniffer Nascimento Ascencio Camargo

et al.

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

Published: Nov. 13, 2024

Herein, we introduce an unprecedented cascade reaction for the assembly of pyrrole-fused 1,5-benzodiazepine frameworks. These diverse privileged scaffolds were controllably constructed by intramolecular cyclization β-enamino diketone, followed annulation with o-phenylenediamine. The protocol features efficient one-pot cyclization/annulation, performed under simple and mild conditions. products are obtained in a metal-free manner, good to excellent yields (65–91%), represent fused heterocyclic scaffold that is not yet found nature.

Language: Английский

Citations

0