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Paper | Special issue | Vol 61, No. 1, 2003, pp.197-223
Published online, 4th August, 2003
DOI: 10.3987/COM-03-S20
Transformations of Alykl (5-Oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetates into 5-Heteroaryl-3-oxo-2-phenyl-3,5-dihydro-2H-pyrazolo[4,3-c]pyridine-7-carboxylates

David Bevk, Renata Jakse, Jurij Svete,* Amalija Golobic, Ljubo Golic, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia

Abstract

Alkyl [(Z)-4-dimethylaminomethylidene-5-oxo-1-phenyl-4,5-dihydro- 1H-pyrazol-3-yl]acetate (4) was transformed with N- and C-nucleophiles into alkyl [4-(substituted amino)methylidene-4,5-dihydro-1H-pyrazol-3-yl]acetates (7) and alkyl (4-heteroarylmethylidene-4,5-dihydro-1H-pyrazol-3-yl)acetates (8), respectively. Compounds (7) cyclize by heating with DMFDMA in DMF into 2H- pyrazolo[4,3—c]pyridine-7-carboxylates (9).