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Paper | Special issue | Vol 70, No. 1, 2006, pp.235-248
Published online, 29th August, 2006
DOI: 10.3987/COM-06-S(W)11
Pyran-2-ones as Synthons for Pyridazine-3-carboxylic Derivatives. Oxidation of Nitrogen-Rich Compounds

Franc Pozgan, Stanislav Kafka, Slovenko Polanc, and Marijan Kočevar*

*Department of Organic Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SI-1000 Ljubljana, Slovenia

Abstract

The reaction of 6-(pyridin-2-yl)-2H-pyran-2-one (1) with hydrazine hydrate toward pyridazine derivatives was investigated. To elucidate the reaction pathway, an intermediary-formed α,β-dihydrazonohydrazide derivative (3) was successfully isolated. Oxidations of the above compounds as well as of other pyridazine derivatives containing a carbohydrazido group, using ammonium cerium(IV) nitrate (CAN), thallium(III) nitrate trihydrate (TTN), or copper(II) acetate hydrate (CuDA), are also presented.