Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure–activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.

Rh(i)-Catalyzed intramolecular [2 + 2 + 1] cycloaddition of diynes with the N-terminal of the diazo group

A Rh(i) catalyzed [2 + 2 + 1] cycloaddition of intramolecular diynes and a diazo moiety has been reported, in which the dediazoniation does not occur and the terminal nitrogen of the diazo moiety serves as the N1 unit.

Mechanistic investigation-inspired activation mode of DBU and the function of the α-diazo group in the reaction of the α-amino ketone compound and EDA: [DBU-H]+-DMF-H2O and α-diazo as strong N-terminal nucleophiles

DFT calculations disclosed a dramatic electronic turnover of the α-diazo group based on an unexpected DBU activation mode.

Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

The sensitized photoexcitation of 2-diazocyclopentane-1,3-diones in the presence of THF leads to the insertion of the terminal N-atom of the diazo group into the α-С–Н bond of THF, producing the associated N-alkylhydrazones in yields of up to 63–71%. Further irradiation of hydrazones derived from furan-fused tricyclic diazocyclopentanediones culminates in the cycloelimination of furans to yield 2-N-(alkyl)hydrazone of cyclopentene-1,2,3-trione. By contrast, the direct photolysis of carbocyclic diazodiketones gives only Wolff rearrangement products with up to 90–97% yield.

The covalently bound diazo group as an infrared probe for hydrogen bonding environments

The bandwidth or position of diazo groups can probe the polarizability and HBA, or density of HBD groups.