Addition reactions of heterocyclic compounds. Part XXV. Dimethyl acetylenedicarboxylate with pyridazines and pyrazines
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 2218-2222
- https://doi.org/10.1039/j39660002218
Abstract
Dimethyl acetylenedicarboxylate in acetonitrile with pyridazine, 3-methylpyridazine, and 1-methylphthalazine gave pyrido[1,2-b]pyridazines, with smaller amounts of related pyrrolo[1,2-b]pyridazines. 3,6-Dimethylpyridazine, however, gave mostly an azepino[1,2-b]pyridazine. 2-Methyl- and 2,6-dimethyl-pyrazines gave only low yields of pyrrolo[1,2-a]pyrazines under these conditions. In methanol, phthalazine gave 1,2-dihydro-1-methoxy-2-(1,2-dimethoxycarbonylvinyl)phthalazine, and phenazine gave 5,10-dihydro-5,10-di-(1,2-dimethoxycarbonylvinyl)phenazine. The nuclear magnetic resonance and ultraviolet absorption spectra of these adducts and their transformation products are discussed.Keywords
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