Synthesis of Indazole Fused 2-Benzazepines with Polarity-Dependent Fluorescence Based on Formal [4 + 3] Annulation of 3-Aryl-1H-indazoles with Cyclopropenones DOI

Qianting Zhou,

Xu Haiyun,

Chang Gao

et al.

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

Published: April 3, 2025

The effective assembly of benzazepine skeletons in a sustainable and atom-economical fashion remains challenging goal modern organic synthesis. Presented herein is novel synthesis indazole fused 2-benzazepine derivatives based on formal [4 + 3] annulation 3-aryl-1H-indazoles with cyclopropenones. formation products proceeds through Ir(III)-catalyzed aryl C-H bond metalation cyclopropenone ring-opening leading to acylation, followed by an intramolecular N-nucleophilic conjugated addition. By using this method, number valuable were effectively generated. This protocol addresses the challenges constructing medium-sized rings cascade C-H/C-C activation C-C/C-N formation. Moreover, photophysical properties thus obtained also evaluated. It turned out that all compounds tested showed solvent polarity-dependent fluorescence features, which could be potentially applied for revealing polarity their immediate environments.

Language: Английский

Divergent Synthesis of Four Types of Fused N‐Containing Heterocycles via Oxidative Multi‐Component Cyclization Reaction DOI Open Access

Xiaoshuang Guo,

Maozhong Miao, Peng Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Comprehensive Summary An atmospheric‐oxygen‐mediated four‐component reaction was developed for the divergent synthesis of pyrazolo[1,5‐ a ]pyrimidine and pyrazolo[3,4‐ b ]pyridine derivatives from readily available alcohols 3‐aminopyrazoles. In this transformation, atmospheric oxygen serves as green oxidant, promoting equivalent aldehydes four types N ‐containing heterocycles (> 40 examples). Remarkably, transformation features metal‐free molecular diversity.

Language: Английский

Citations

4
Palladium-catalyzed intermolecular formal [3+2] cyclization/C-H alkylation of polyfluoroarenes DOI
Zhongyao Jiang, Chenglin Liu,

Mingxia Wu

et al.

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

Published: Jan. 1, 2025

A sequential three-component intermolecular carbopalladation/Heck cyclization/intermolecular C–H bond functionalization for versatile alkylated polyfluoroarenes containing an indene skeleton is presented.

Language: Английский

Citations

0
Direct Access to CF3-Containing 4H-1,3-Oxazines and 2-Aminopyrimidines Via a [4 + 2] Annulation Using In Situ Generated Carbodiimide Anions DOI
Huamin Wang,

Wenjing Niu,

Wei Min

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The carbodiimide anions which were generated in situ from N-cyano-N-aryl-p-toluenesulfonamides (NCTS) the presence of base participated annulations that remain less reported to date. Herein, we have developed for first time an efficient and environmentally friendly [4 + 2] annulation reaction CF3-substituted hetero-1,3-dienes with NCTS synthesis 4H-1,3-oxazines 2-aminopyrimidines under transition-metal-free conditions. methodology demonstrates advantages readily available substrates, simple operation, good functional group tolerance, broad substrate scope, providing a promising route structurally diverse scaffolds. products followed by transformations provide facile TAS2R14 agonist analogues.

Language: Английский

Citations

0
Condition‐Controlled Selective Synthesis of CF3‐Chromene and CF3‐Benzofuran from N‐Phenoxyacetamide and CF3‐Ynone DOI Open Access

Huihang Hou,

Shengnan Yan,

Yuanshuang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

Citations

0
Synthesis of Indazole Fused 2-Benzazepines with Polarity-Dependent Fluorescence Based on Formal [4 + 3] Annulation of 3-Aryl-1H-indazoles with Cyclopropenones DOI

Qianting Zhou,

Xu Haiyun,

Chang Gao

et al.

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

Published: April 3, 2025

The effective assembly of benzazepine skeletons in a sustainable and atom-economical fashion remains challenging goal modern organic synthesis. Presented herein is novel synthesis indazole fused 2-benzazepine derivatives based on formal [4 + 3] annulation 3-aryl-1H-indazoles with cyclopropenones. formation products proceeds through Ir(III)-catalyzed aryl C-H bond metalation cyclopropenone ring-opening leading to acylation, followed by an intramolecular N-nucleophilic conjugated addition. By using this method, number valuable were effectively generated. This protocol addresses the challenges constructing medium-sized rings cascade C-H/C-C activation C-C/C-N formation. Moreover, photophysical properties thus obtained also evaluated. It turned out that all compounds tested showed solvent polarity-dependent fluorescence features, which could be potentially applied for revealing polarity their immediate environments.

Language: Английский

Citations

0