Double retro Diels-Alder reaction applied for preparation of a pyrimido[1,2-b]pyridazine

Ferenc Miklós, Géza Stájer, Pál Sohár, Zsolt Böcskei

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Boiling diendo- or diexo-2-aminobicyclo[2.2.1]hept-5-ene-3- carbohydrazides 1 with 3-aroylnorbornenecarboxylic acid 2 in toluene yielded the pyrimido[1,2-b]pyridazine 4 directly in a double retro Diels-Alder process. Similarly, the reaction of anthranilic hydrazide 5 and 2 furnished the tricyclic benzo-fused analogue 7 via a single cycloreversion. The principle of the new method applied: the reactants were built up on cyclopentadienes and the dienes were cleaved by heating after condensation to furnish hetero bicyclic compound.

Original languageEnglish
Pages (from-to)67-68
Number of pages2
JournalSynlett
Issue number1
Publication statusPublished - Jan 1 2000

Keywords

  • Double cycloreversion
  • Pyrimidopyridazine
  • Retro Diels-Alder
  • Synthetic panels
  • Thermal splitting

ASJC Scopus subject areas

  • Organic Chemistry

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