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Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Author(s) -
Annatelli Mattia,
Trapasso Giacomo,
Salaris Claudio,
Salata Cristiano,
Castellano Sabrina,
Aricò Fabio
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100328
Subject(s) - chemistry , moiety , organic chemistry , chlorine , reagent , alcohol , yield (engineering) , carbonate , combinatorial chemistry , phenols , metallurgy , materials science
Abstract N,N ‐dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one‐pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β‐aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β‐aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.