1022-88-4

Upstream product

• 52548-63-7 5-fluoro-2-iodobenzoic acid 
• 62-53-3 aniline 
• 394-28-5 2-Bromo-5-fluorobenzoic acid 

Downstream Products

• 1428865-16-0 C₁₅H₁₄FNO₂ 
• 1096880-62-4 5-fluoro-2-(methyl(phenyl)amino)benzaldehyde 
• 1096862-17-7 C₁₄H₁₄FNO 
• 1239702-58-9 5-fluoro-N-(4-(3-(2-methylaminopyrimidin-4-yl)pyridin-2-yloxy)phenyl)-2-phenylaminobenzamide 

Relevant academic research and scientific papers

Redox-neutral decarboxylative photocyclization of anthranilic acids

A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones

A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.