389634-83-7

Upstream product

• 111-71-7 heptanal 
• 621-37-4 m-hydroxyphenylacetic acid 
• 109-73-9 N-butylamine 
• 389634-82-6 3-(4-fluoro-3-nitrophenyl)-2-isocyanopropionic acid ethyl ester 
• 459-57-4 4-fluorobenzaldehyde 
• 389634-80-4 2-(4-fluoro-3-nitro-benzyl)-2-formylamino-malonic acid diethyl ester 
• 15017-52-4 4-(bromomethyl)-1-fluoro-2-nitrobenzene 
• 20274-69-5 (4-fluoro-3-nitrophenyl)methanol 
• 389634-81-5 3-(4-fluoro-3-nitro-phenyl)-2-formylamino-propionic acid ethyl ester 
• 42564-51-2 4-fluoro-3-nitrobenzaldehyde 

Relevant academic research and scientific papers

Rapid and diverse route to natural product-like biaryl ether containing macrocycles

A two-step sequence involving an Ugi four-component reaction and an intramolecular nucleophilic aromatic substitution (SNAr) has been developed for the rapid access to biaryl-ether containing macrocycles. In the course of this study, we documented that ammonium chloride can promote the Ugi-4CR in non-polar aprotic solvent (toluene) without the interference of an alternative Passerini reaction. Solid phase synthesis of macrocycles by this two-step sequence was also developed using polymer (Wang resin) supported α-(4′-fluoro-3′-nitro)phenethyl isocyanoacetate as one of the inputs.

A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based cycloetherification.

[reaction: see text] From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular S(N)Ar reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride in aprotic solvent is documented for the first time.