Palladium-catalyzed synthesis of 4-aminophthalazin-1(2H)-ones by isocyanide insertion

Tjøstil Vlaar; Eelco Ruijter; Anass Znabet; Elwin Janssen; Frans J J de Kanter; Bert U W Maes; Romano V A Orru

doi:10.1021/ol202784d

Palladium-catalyzed synthesis of 4-aminophthalazin-1(2H)-ones by isocyanide insertion

Org Lett. 2011 Dec 16;13(24):6496-9. doi: 10.1021/ol202784d. Epub 2011 Nov 15.

Authors

Tjøstil Vlaar¹, Eelco Ruijter, Anass Znabet, Elwin Janssen, Frans J J de Kanter, Bert U W Maes, Romano V A Orru

Affiliation

¹ Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

PMID: 22085248
DOI: 10.1021/ol202784d

Abstract

Palladium-catalyzed cross-coupling of a wide range of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion followed by lactamization efficiently affords 4-aminophthalazin-1(2H)-ones that are difficult to obtain regioselectively by classical methods.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Nitriles / chemistry*
Nitriles / pharmacology*
Palladium / chemistry*
Phthalazines / chemical synthesis*
Phthalazines / chemistry
Stereoisomerism

Substances

4-aminophthalazin-1(2H)-one
Nitriles
Phthalazines
Palladium