71675-75-7

Upstream product

• 771-97-1 2,3-Diaminonaphthalene 
• 1792-36-5 1H-2-methylnaphtho[2,3-d]imidazole 
• 74-88-4 methyl iodide 

Downstream Products

• 4572-59-2 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione 

Relevant academic research and scientific papers

Induction-driven stabilization of the anion-π interaction in electron-rich aromatics as the key to fluoride inclusion in imidazolium-cage receptors

Intermolecular interactions that involve aromatic rings are key processes in both chemical and biological recognition. It is common knowledge that the existence of anion-π interactions between anions and electron-deficient (π-acidic) aromatics indicates that electron-rich (π-basic) aromatics are expected to be repulsive to anions due to their electron-donating character. Here we report the first concrete theoretical and experimental evidence of the anion-π interaction between electron-rich alkylbenzene rings and a fluoride ion in CH3CN. The cyclophane cavity bridged with three naphthoimidazolium groups selectively complexes a fluoride ion by means of a combination of anion-π interactions and (Ci?￡?H) +?F--type ionic hydrogen bonds. 1H NMR, 19F NMR, and fluorescence spectra of 1 and 2 with fluoride ions are examined to show that only 2 can host a fluoride ion in the cavity between two alkylbenzene rings to form a sandwich complex. In addition, the cage compounds can serve as highly selective and ratiometric fluorescent sensors for a fluoride ion. With the addition of 1 equiv of F-, a strongly increased fluorescence emission centered at 385 nm appears at the expense of the fluorescence emission of 2 centered at 474 nm. Finally, isothermal titration calorimetry (ITC) experiments were performed to obtain the binding constants of the compounds 1 and 2 with F- as well as Gibbs free energy. The 2-F- complex is more stable than the 1-F- complex by 1.87 kcal mol-1, which is attributable to the stronger anion-π interaction between F- and triethylbenzene.

Oxidation products of fused 2-hetarylimidazole derivatives

Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1- methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)- hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro- [9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. ?-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen. Pleiades Publishing, Ltd., 2011.

6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof

Antibacterial penicillins of the formula STR1 or a pharmaceutically acceptable salt thereof wherein R1 is a heterocyclic group and R is hydrogen, the residue of certian carboxy protecting groups or the residue of an ester group readily hydrolyzable in vivo having activity against resistant organisms.