Abstract
Diarylmethanes (DAMs) and triarylmethanes (TAMs) are molecules with two or three aryl groups (phenyls or heterocycles) bonded to a central carbon atom and they have numerous applications. The biological and therapeutic relevancy of this class of molecules have been demonstrated in diverse areas such as antimicrobials, infectious, cardiovascular and nervous system disorders, genital tract diseases, estrogen related disorders and bone remodeling is quite well known. These interesting compounds have also been used as starting materials for the development of high value added molecules. Several synthetic approaches towards bioactive diarylmethanes and triarylmethanes have been published in the literature. This article reviews some approaches followed for the synthesis of diarylmethanes and triarylmethanes as well their biological applications. We will also illustrate the synthesis and antibacterial evaluation of a new triarylmethane series developed in our laboratory using McMurry coupling reaction.
Highlights
Di- and tri-arylmethanes have attracted much attention as a result of their unique structural and physical properties and applications in organic chemistry and as interesting scaffolds presented in biological active compounds [1,2].The feature of triarylmethane compounds comes from the three aryl groups bonded to a sp3 hybridized central carbon atom bearing a hydrogen atom
Diarylmethane scaffold is mainly obtained by Friedel–Crafts alkylation of the corresponding benzyl alcohols with another arene, metalcatalyzed cross coupling of aryl halides with benzyl nucleophiles, metal catalyzed cross coupling of benzyl halides with aryl nucleophiles and C–C bond formation between tosyl hydrazones and aryl boronic acids [1]
Diarylmethanes were prepared via a McMurry coupling reaction
Summary
Di- and tri-arylmethanes have attracted much attention as a result of their unique structural and physical properties and applications in organic chemistry and as interesting scaffolds presented in biological active compounds [1,2].The feature of triarylmethane compounds comes from the three aryl groups bonded to a sp hybridized central carbon atom bearing a hydrogen atom. Diarylmethane scaffold is mainly obtained by Friedel–Crafts alkylation of the corresponding benzyl alcohols with another arene, metalcatalyzed cross coupling of aryl halides with benzyl nucleophiles, metal catalyzed cross coupling of benzyl halides with aryl nucleophiles and C–C bond formation between tosyl hydrazones and aryl boronic acids [1]. Considering this perspective, we presented in this paper the synthesis of two diarylmethanes using a McMurry cross coupling reaction. We describe the synthesis of two new diarylmethanes derivatives: 4-methoxyphenyl-2arylvinyl-pyridine and its ferrocenyl analogue and the preliminary evaluation of their antibacterial activity
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