By the same authors

From the same journal

From the same journal

Tandem Horner-Wadsworth-Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

Department/unit(s)

Publication details

JournalTetrahedron
DatePublished - 14 Aug 2010
Issue number33
Volume66
Number of pages7
Pages (from-to)6606-6612
Original languageEnglish

Abstract

A tandem sequence involving Horner-Wadsworth-Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from alpha-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability of the process has been established by carrying out one-pot syntheses of Semaxanib, an angiogenesis signalling inhibitor, and GW441756, an aza-oxindole Trk A inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

    Research areas

  • Heck, Horner-Wadsworth-Emmons, Phosphonates, Palladium catalysis, Oxindoles, Tandem reactions, Semaxanib, GW441756, INTRAMOLECULAR HECK REACTION, PALLADIUM-CATALYZED CYCLIZATION, C-H FUNCTIONALIZATION, KINASE INHIBITORS, 3-SUBSTITUTED INDOLIN-2-ONES, OXINDOLES, DISCOVERY, CYCLOADDITION, DERIVATIVES, INDOLES

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations