59816-85-2

Usage

Class

Anilines

Uses

Synthesis of pharmaceuticals and agrochemicals, production of dyes and other organic compounds

Applications

Wide range of applications in organic synthesis

Caution

Handle with care, prolonged exposure or high concentrations can be harmful

Upstream product

• 117531-37-0 N-allyl-3-methoxyaniline 
• 536-90-3 m-Anisidine 
• 848492-86-4 1-allyl-4-methoxy-2-nitrobenzene 

Downstream Products

• 1094358-96-9 N-(2-allyl-5-methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 1380538-80-6 (S)-2-(iodomethyl)-6-methoxy-1-tosylindoline 
• 1211480-91-9 N,2-diallyl-5-methoxyaniline 

Relevant academic research and scientific papers

Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer

Problem solved: The title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines (see scheme). Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence. Copyright

Highly stereoselective 7-endo-trig /ring contraction cascade to construct pyrrolo[1,2- a ]quinoline derivatives

With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the γ-lactam ring and electron-rich arene are important driving forces for ring contraction.

Boron trifluoride-diethyl ether complex catalyzed aromatic amino-Claisen rearrangements

Boron trifluoride-diethyl ether complex (BF3 · OEt2) was demonstrated to be an efficient catalyst for the amino-Claisen rearrangements of various aromatic N-allylamines into the corresponding o-allylamines in moderate yields.

A concise synthesis of a benzimidazole analogue of mycophenolic acid using a BF3-Et2O catalyzed amino-Claisen rearrangement

A nine-step synthesis of the benzimidazole analogue, 2, of mycophenolic acid is reported involving both the BF3-Et2O catalyzed aromatic amino- and the ortho ester Claisen rearrangements as key steps.