Abstract
Xanthene and Xanthenediones are structural components of several bioactive and semi-synthetic molecules. This work described an expeditious synthesis of novel and hitherto unreported bis-trifluoromethyl xanthene dione derivatives. The reaction of two equivalents of 5-trifluoromethyl cyclohexane-1,3- dione with substituted aromatic aldehydes in the presence of ethanol containing 1 - 2 drops of HCl was facile under microwave irradiation. Short reaction time (25 min), good to excellent yields (80% - 95%), good atom economy, and simple workup are the major advantages of the above procedure. Moreover, the fluorinated products represent synthetically useful stable intermediates that could find applications in pharmaceutical, agricultural and material industries.
Highlights
IntroductionSeveral reports of 9-phenyl substituted xanthenedione derivatives containing bis-methyl, ethyl, isopropyl, phenyl and hydrogen have appeared in the literature [1] [2] [3] [4], the corresponding bis-trifluoromethyl group have received little or no attention
The reaction of two equivalents of 5-trifluoromethyl cyclohexane-1,3dione with substituted aromatic aldehydes in the presence of ethanol containing 1 - 2 drops of HCl was facile under microwave irradiation
Several reports of 9-phenyl substituted xanthenedione derivatives containing bis-methyl, ethyl, isopropyl, phenyl and hydrogen have appeared in the literature [1] [2] [3] [4], the corresponding bis-trifluoromethyl group have received little or no attention
Summary
Several reports of 9-phenyl substituted xanthenedione derivatives containing bis-methyl, ethyl, isopropyl, phenyl and hydrogen have appeared in the literature [1] [2] [3] [4], the corresponding bis-trifluoromethyl group have received little or no attention. The introduction of a phenyl sulfonamide at the above position gave rise to derivatives with antimicrobial [9] [10], antimalarial [11] [12], and antibacterial activities [13] [14] [15] [16]. A survey of the literature showed that a typical procedure for the preparation of xanthenes and their 1,8-dioxo derivatives involved the well-known multicomponent reaction of a cyclic β-diketone with substituted aromatic aldehydes under a variety of reaction conditions. The above was achieved via condensation of our previously reported 5-trifluorome-thylcyclohexane-1,3-dione with substituted aromatic aldehydes under conventional heating and microwave irradiation
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