5059-82-5Relevant articles and documents
SALICYLIC ACID SULFONYL DERIVATIVES AND RELATED COMPOUNDS
Cremlyn, Richard,Swinbourne, Frederick,Plant, Stephen,Saunders, David,Sinderson, Colin
, p. 323 - 332 (2007/10/02)
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).
