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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

Catalyst-free Synthesis of Aminomethylphenol Derivatives in Cyclopentyl Methyl Ether via Petasis Borono-Mannich Reaction

Author(s): Jia-Qi Di, Hao-Jie Wang, Zhen-Shui Cui, Jin-Yong Hu* and Zhan-Hui Zhang*

Volume 18, Issue 3, 2021

Published on: 16 December, 2020

Page: [294 - 300] Pages: 7

DOI: 10.2174/1570179417666201216161143

Price: $65


Objective: Aminomethylphenol molecules have wider applications in pharmaceuticals, agrochemicals, plant protection and promising functional materials. The development of an efficient and practical method to prepare this class of compound is highly desirable from both environmental and economical points of view.

Materials and Methods: In order to establish an effective synthetic method for preparing aminomethylphenol derivatives, the Petasis borono-Mannich reaction of salicylaldehyde, phenylboronic acid and 1,2,3,4- tetrahydroisoquinoline was selected as a model reaction. A variety of reaction conditions are investigated, including solvent and temperature. The generality and limitation of the established method were also evaluated.

Results and Discussion: It was found that model reaction can be carried out in cyclopentyl methyl ether at 80 °C under catalyst-free conditions. This protocol, with broad substrate applicability, the reaction of various arylboronic acid, secondary amine and salicylaldehyde proceeded smoothly under optimal reaction conditions to afford various aminomethylphenol derivatives in high yields. A practical, scalable, and high-yielding synthesis of aminomethylphenol derivatives was successfully accomplished.

Conclusion: A catalyst-free practical method for the synthesis of minomethylphenol derivatives based on Petasis borono–Mannich (PBM) reaction of various arylboronic acid, secondary amine and salicylaldehyde in cyclopentyl methyl ether has been developed. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of cyclopentyl methyl ether as the reaction medium, clean reaction profiles, easy operation, and high to excellent yield.

Keywords: Catalyst-free, cyclopentyl methyl ether, green synthesis, minomethylphenol derivatives, multicomponent reactions, Petasis borono– Mannich reaction.

Graphical Abstract
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