A new approach to the synthesis of 4-(N-aryl)carbamoylmethyl-4,5-dihydropyridazin-3(2H)-ones

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Abstract

Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2H)-ones is demonstrated for the first time. 2011 Published by Elsevier Ltd.
Original languageEnglish
Pages (from-to)3146–3149
JournalTetrahedron Letters
Volume52
DOIs
StatePublished - 2011

Keywords

  • N-Arylmaleimides Aliphatic ketazines 4
  • 5-Dihydropyridazin-3(2H)-ones Solvent-free conditions Microwave irradiation Michael addition product

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