Multicomponent Synthesis of 4-Aminophthalazin-1(2H)-ones by Palladium-Catalyzed Isocyanide Insertion

T. Vlaar, P. Mampuys, M. Helliwell, B.U.W. Maes, R.V.A. Orru, E. Ruijter

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

4-Aminophthalazin-1(2H)-ones (APOs) are underexplored heterocyclic compounds with promising and diverse biological activities. The classical synthesis of these compounds is tedious and does not allow the regioselective introduction of substituents. Here, we present our full studies on the Pd-catalyzed cross-coupling of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion allowing straightforward access to diversely substituted APOs. We illustrate the advantages of this method compared to other approaches and describe solutions for the limitations we encountered. In addition, we have developed efficient diversifications of this heterocyclic scaffold that allow access to more diverse APOs as well as novel heterocyclic scaffolds. © 2013 American Chemical Society.
Original languageEnglish
Pages (from-to)6735-674
JournalJournal of Organic Chemistry
Volume2013
Issue number78
DOIs
Publication statusPublished - 2013

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