Microwave-Assisted Synthesis of 3,6-Di(pyridin-2-yl)pyridazines: Unexpected Ketone and Aldehyde Cycloadditions

R. Hoogenboom, B.C. Moore, U.S. Schubert

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Scopus)

Abstract

3,6-Di(pyridin-2-yl)pyridazines are an interesting class of compds. because of their metal-coordinating ability resulting in the self-assembly into [2*2] gridlike metal complexes with copper(I) or silver(I) ions. These and other substituted pyridazines can be prepd. by the inverse-electron-demand Diels-Alder reactions between acetylenes and 1,2,4,5-tetrazines. In this contribution, the effect of (superheated) microwave conditions on these generally slow cycloaddns. is described. The cycloaddn. of acetylenes to 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine could be accelerated from several days reflux in toluene or N,N-dimethylformamide to several hours in dichloromethane at 150 DegC. In addn., the unexpected cycloaddn. of the enol tautomers of various ketones and aldehydes to 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine is described in detail providing an alternative route for the synthesis of (substituted) pyridazines. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)4903-4909
Number of pages7
JournalJournal of Organic Chemistry
Volume71
Issue number13
DOIs
Publication statusPublished - 2006

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