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.
Original language | English |
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Pages (from-to) | 6606-6612 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 66 |
Issue number | 33 |
DOIs | |
Publication status | Published - 14 Aug 2010 |
Keywords
- 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