2408-99-3

Upstream product

• 98-88-4 benzoyl chloride 
• 3989-50-2 4-acetamidobenzenesulfonylhydrazine 
• 613-94-5 benzoic acid hydrazide 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Downstream Products

• 84907-37-9 N-benzoyl-N'-sulfanilyl-hydrazine 

Relevant academic research and scientific papers

Synthesis of sulfanilamido-naphthoquinones as potential antituberculous agents

p-Aminobenzoic acid, the acid hydrazides of benzoic acid, salicylic acid and isonicotinic acid, and 4,4'-diaminodiphenyl sulfone were condensed with p-aminobenzenesulfonyl chloride to give the corresponding N1-substituted sulfanilamides. These molecules were then treated with 1,4-naphthoquinone to yield 2-substituted-1,4-naphthoquinones. The partition coefficient for the substituted quinones showed, in some cases, high diffusion rates to the organic phase, benzene, from physiological Tyrode's solution. These compounds are effective in low concentration in dioxane against the human sensitive strain of Mycobacterium tuberculosis H37 Rv. Sulfanilamides obtained from p-aminosalicylic acid and thiosemicarbazide failed to react with 1,4-naphthoquinone. These sulfanilamides also showed high activity against the same Mycobacterium.

SALICYLIC ACID SULFONYL DERIVATIVES AND RELATED COMPOUNDS

Salicylic acid-5-sulfonohydrazide (3) has been condensed with β-dicarbonyl compounds to form pyrazoles (5).With ethyl acetoacetate, tri- and hexafluoropentane-2,4-dione the hydrazones (4) were obtained; although the former did cyclise in the presence of potassium carbonate-magnesium sulfate.With hexane-2,5-dione the pyrrole (7) was formed and not the pyridazine (8).Acylation of salicylic acid-5- and p-acetamidobenzene-sulfonohydrazides was examined; mono-acetates, benzoates and p-toluenesulfonates and diacetates are described, but other pure diacyl derivatives could not be i solated.Reaction with succinic and maleic anhydrides gave the corresponding amic acids (9, 10), and their cyclisation to pyridazines (11) was examined; only the maleamic acid (10) was converted to the pyridazine (11).Maleic hydrazide (14) by condensation with p-acetamido-benzenesulfonyl chloride gave the O-sulfonyl pyridazine (15). 5-Chlorosalicylic acid-3-sulfonohydrazide (18) was prepared and characterized as the acetone and cyclohexanone hydrazones (19); but attempts to make aromatic hydrazones gave the azines (20). 5-Chlorosalicylic acid-3-sulfonyl azide (21) reacted with norbornene and triphenylphosphine to give the aziridine (22) and the phosphinimine (23).