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Domino reactions of 4,5-dicyanopyridazine with dihydroheterocycles: synthetic and mechanistic features

, : Domino reactions of 4,5-dicyanopyridazine with dihydroheterocycles: synthetic and mechanistic features. Journal of Organic Chemistry 68(8): 3340-3343

The title pyridazine 1 was found to react with both 2,3-dihydrofuran (2) and 3,4-dihydro-2H-pyran (9) to give the tetracyclic skeletons 5-8 and the phthalonitrile 12 through the intermediates 4 and 10, respectively. A more complex mechanism was ascertained for the reaction of 1 with the pyrroline 14 which, under suitable conditions, afforded the bicyclic derivative 19 as the predominant product; selective elaborations of this species into the 5,6-dicyanoindoles 22 and 23 are reported.


PMID: 12688817

DOI: 10.1021/jo026761x

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