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Terminal versus Internal Diiodobenzyl Alcohol Derivatives via Regioselective Metal–Iodine Exchange of 1,2,3‐Triiodoarenes: Synthesis and Antibacterial Activity
Author(s) -
AlZoubi Raed M.,
AlZoubi Mazhar S.,
Abazid Ayham H.,
McDonald Robert
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402288
Subject(s) - regioselectivity , micrococcus luteus , serratia marcescens , chemistry , antibacterial activity , alcohol , organic chemistry , escherichia coli , combinatorial chemistry , catalysis , bacteria , biochemistry , genetics , biology , gene
Abstract A wide range of unique diiodobenzyl alcohol building blocks have been synthesized by regioselective metal‐iodine exchange (MIE) reactions using isopropylmagnesium chloride is reported. Remarkably, the regioselectivity of the MIE reaction is easily controlled by both the aldehydes and the 1,2,3‐triiodoarenes to provide either the internal or the terminal products in good yields and in a highly regioselective fashion. The synthesized diiodobenzyl alcohols were tested for in vitro antibacterial activity against two Gram‐positive strains, Micrococcus luteus (ATCC 934) and Staphylococcus aureus (ATCC 29213), and two Gram‐negative strains, Escherichia coli (ATCC 25922) and Serratia marcescens (ATCC 27117). The biological data clearly shows that all tested diiodobenzyl alcohols have selective antibacterial activity against Gram‐positive strains and no activity against Gram‐negative ones. This report discloses a facile protocol for the synthesis of hitherto unknown ortho ‐diiodobenzyl alcohol and 2,3‐diiodobenzyl alcohol derivatives in only one step that is quite general in scope and scalable, with products that are hard to make by any other means.