A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, sh...

The first synthesis of 4 ́-X-phenylverbenene (X = F and Cl) via reaction of myrtenal with 4 -X phenylmagnesium bromide and Bi(NO3)3 is described. Verbenene is formed due to the electron-withdrawing effect of the 4 electronegative group, either fluorine or a Cl–Bi complex.

An electron-withdrawing group was introduced to the α-position of chalcones, and the resulting alkylidene diketones showed new reactivities with enals under the catalysis of N-heterocyclic carbenes (NHCs). Selective activation of enals affords enolate equivalents that undergo highly enantioselective intermolecular Diels-Alder reactions with the alkylidene diketones. No products that might have ...

Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron-withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has...

Ratiometric fluorescent probes based on boron dipyrromethene (BODIPY) were developed based on a novel design strategy, in which a change of the electron-withdrawing character of the 2,6-substituents resulting from reaction with a target molecule generates a fluorescence wavelength change.

To investigate the effects of electron-donating and electron-withdrawing substituents upon the reaction of porphyrins with osmium tetraoxide, and the pinacol-pinacolone rearrangement of the resulting diols, a series of meso-substituted porphyrins were prepared by total synthesis. Porphyrins with electron-donating substitutents at the meso-positions gave vic-dihydroxychlorins in which the adjace...

An efficient method for the synthesis of 5-substituted-1H-tetrazoles through the reaction of nitriles with sodium azide using titanium oxide–supported boric acid (TiO2-H3BO3) catalyst was reported. The reactions were carried out at 120 °C and provided the corresponding tetrazoles in good to excellent yields. This method displayed significant advantages ...

An efficient method for the synthesis of 5-substituted-1H-tetrazoles through the reaction of nitriles with sodium azide using titanium oxide–supported boric acid (TiO2-H3BO3) catalyst was reported. The reactions were carried out at 120 °C and provided the corresponding tetrazoles in good to excellent yields. This method displayed significant advantages ...

A modified dumbbell obtained by replacing one of the phenyl groups of the dibenzylammonium with a strong electron-withdrawing trifluoromethyl group templated the synthesis of the smallest [2]rotaxane reported so far. The trifluoromethyl group not only enhances the templating effect of the dumbbell but also acts as the stopper to prevent dethreading of a [20]crown ether macrocycle.

A series of non-Grignard Mg-electrolytes with various para-substituents was synthesized starting from commercially-available phenols. More electron-withdrawing substituents shift the anodic stability of the electrolyte by 400 mV. The p-CF3 substituted phenol exhibits the highest stability of 2.9 V vs. Mg(2+/0), and cycles reversibly with the Chevrel-phase Mo6S8 Mg-ion cathode.