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Issue 5, 1975
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Addition reactions of heterocyclic compounds. Part LVIII. Reactions of nitrogenous heterocycles with acetylacetylene

R. Morrin Acheson  and  John Woollard 

Abstract

Simple pyridines react with acetylacetylene and proton donors at –20° to give high yields of (E)-1-(3-oxobut-1-enyl)-1,4-dihydropyridines, while in the absence of such donors low yields of other compounds are isolated. Acetylacetylene reacts with 4-aminopyridine to give 4-[(E)-3-oxobut-1-enylimino]-1,4-dihydropyridine, imidazoles give the 1-[(E)-3-oxobut-1-enyl] derivatives, methyl 2-pyridylacetate yields quinolizines, and pyrrole the 2-[(E)-3-oxobut-1-enyl] derivative and 4,6-diacetylindole. The structures of these products and of minor components, are deduced mainly from their n.m.r. spectra.

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Article type: Paper
DOI: 10.1039/P19750000446
Citation: J. Chem. Soc., Perkin Trans. 1, 1975,0, 446-451
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    Addition reactions of heterocyclic compounds. Part LVIII. Reactions of nitrogenous heterocycles with acetylacetylene

    R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans. 1, 1975, 0, 446
    DOI: 10.1039/P19750000446

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