Abstract
Herein, we report the approach to the otherwise hardly accessible dibenzoxanthenes, diarylbutanes, and calix[4]resorcinarenes possessing urea moieties based on the reaction of N-(4,4-diethoxybutyl)ureas with electron-rich aromatics in strongly acidic media. Unlike the previously developed methods, the proposed approach benefits from one-pot procedure and allows to obtain the target compounds with much higher yields.
Highlights
Diarylmethane derivatives containing two phenolic moieties are of interest due to their wide spectrum biological activity.ese compounds are known to inhibit C-C chemokine receptors [1], possess anti-inflammatory [2], antiproliferative [3], antimicrobial [4], anti-HIV [5], and anticancer activity [6]
E most general approach to these compounds is the acidic media condensation of electron-rich aromatic nucleophiles with aldehydes [17,18,19] or acetals [20,21,22] (Scheme 1(A)). This method is inapplicable in case of acetals containing urea moiety, since these compounds are subject to intramolecular cyclization in acidic media [23,24,25,26]
We have developed the approach to diarylbutanes, dibenzoxanthenes, and calixarenes possessing urea fragment via acid-catalyzed ring opening of 2-(2hydroxynaphthalene-1-yl)pyrrolidine-1-carboxamides 1
Summary
Diarylmethane derivatives containing two phenolic moieties are of interest due to their wide spectrum biological activity. Ese compounds are known to inhibit C-C chemokine receptors [1], possess anti-inflammatory [2], antiproliferative [3], antimicrobial [4], anti-HIV [5], and anticancer activity [6]. E most general approach to these compounds is the acidic media condensation of electron-rich aromatic nucleophiles with aldehydes [17,18,19] or acetals [20,21,22] (Scheme 1(A)) This method is inapplicable in case of acetals containing urea moiety, since these compounds are subject to intramolecular cyclization in acidic media [23,24,25,26]. Methods allowing “one-pot” synthesis of the target compounds is of a great importance nowadays due to both their effectiveness and atom economy [29], which are among main principles of green chemistry. us, we report the improved one-pot approach to the diarylbutane derivatives containing urea moieties starting from accessible N-(4,4-diethoxybutyl)ureas 2
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