73810-75-0Relevant articles and documents
STUDIES IN THE FIELD OF NITROGEN HETEROCYCLIC COMPOUNDS. PART X. SYNTHESIS AND NEW RING TRANSFORMATION OF SOME FUSED PYRAZOLE SYSTEMS
Balicki, Roman
, p. 1273 - 1278 (2007/10/02)
Condensation of 3-amino-1-methylpyrazole (7) with ethyl acetoacetate (1) in ethanol leads to formation of aminocrotonate 8, whereas the reaction in Dowtherm A above 200 deg C gives acetoacetamide (9).Ring closure of 8 in polyphosphoric acid (PPA) or ethanolic hydrochloride gives pyrazolopyrimidine (10).However, in Dowtherm A besides compound 10, the pyrazolopyridine (11) is also formed.Heating of 10 in Dowtherm A at 220-240 deg C causes ring transformation into 11.In acetic acid, compound 8 undergoes rearrangement to acetoacetamide 9 prior to cyclization into pyrazolopyridine (12).The structures of the compounds obtained were deduced from their IR, MS, 1H NMR and 13C NMR spectra.Pathways of the reactions presented are also discussed.