Double intramolecular Diels–Alder reaction of α,β-unsaturated hydrazones: a new route to 2,2′-bipyridines

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Nicholas Bushby, Christopher J. Moody, David A. Riddick and Ian R. Waldron


Abstract

Heating the 1,3-diynyl bis-α,β-unsaturated hydrazones 3, 6 and 10 results in double intramolecular Diels–Alder reaction of the 1-azadienes, and after aromatisation by loss of dimethylamine, the formation of bipyridines 11–14.


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