70220-83-6

Upstream product

• 89-25-8 edaravone 
• 106-40-1 4-bromo-aniline 
• 100-63-0 phenylhydrazine 
• 18794-98-4 ethyl 2-(2-(4-bromophenyl)hydrazono)-3-oxobutanoate 

Relevant academic research and scientific papers

Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: Design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

Waste-free chemistry of diazonium salts and benign separation of coupling products in solid salt reactions

Gas-solid and solid-solid techniques allow for waste-free and quantitative syntheses in the chemistry of diazonium salts. Five techniques for diazotations with the reactive gases NO2, NO and NOCl are studied. Two types are mechanistically investigated with atomic force microscopy (AFM) and are interpreted on the basis of known crystal packings. The same principles apply to the cascade reactions that had been derived from one-step reactions. Solid diazonium salts couple quantitatively with solid diphenylamine and anilines to give the triazenes. Azo couplings are achieved with quantitative yields by cautious co-grinding of solid diazonium salts with β-naphthol and C-H acidic heterocycles, such as barbituric acids or pyrazolinones. Solid diazonium salts may be more easily applied in a stoichiometric ratio for couplings in solution. Co-grinding of solid diazonium salts with KI gives quantitative yields of various solid aryl iodides. The unavoidable coupling products in salt reactions are completely separated from the insoluble products in a highly benign manner. The solid-state reactions compare favourably with similar solution reactions that produce much waste. The structures of the products are elucidated with IR and NMR spectroscopy and mass spectrometry, while the tautomeric properties of the compounds are studied with density functional calculations at the B3LYP/6-31G* and BLYP/6-31G** levels.

A Simple Route for the Synthesis of Chlorosubstituted Arylazobenzenes, Arylazonaphtalenes, and Arylazopyrazoles

The reaction of arylazophenoles and arylazohydroxypyrazoles (or their tautomer hydrazones) 10, 11, and 15 with POCl3 in dimethylformamide yields chlorosubstituted arylazobenzenes or arylazopyrazoles 12, 13 and 16, resp., in moderate to high yields.The substitution of the OH-group by the Cl-moiety is favoured by acceptor substituents in the aryl fragments ortho- and/or para-linked to the azo group.In case that arylazocompounds derived from resorcinol are used the substitution reaction runs in a stepwise manner giving raise to the formation of o-hydroxy-p-chlorosubstit uted azo compounds 18 primarily and then of dichlorosubstituted azo compounds 19.