Abstract
Abstract The hydrochloride of pyridine-3-sulfonyl chloride (1) with hydrazine gave the hydrazide (2), from which a semicarbazide (15) and a series of hydrazones (4–14) were obtained. The chemical shifts of the NH protons of the hydrazones were correlated with the Hammett [sgrave]-constants of the substituents. With sodium azide, the sulfonyl chloride (1) gave the azide (16) which reacted with both norbornene and triphenylphosphine. The sulfonyl chloride (1) was hydrolysed to the sulfonic acid (3) by boiling with ethanol. Reaction of the hydrazide (2) with β-diketones afforded the pyrazoles (19a–22a). The intermediate sulfonohydrazones (19–22) were isolated in each case; however the product with ethyl acetoacetate (26) could not be cyclised to the pyrazole. The mass spectra of the pyrazoles are briefly discussed.
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