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

被引：38
作者：
Lubkoll, Jana [1 ]
Millemaggi, Alessia [1 ]
Perry, Alexis [1 ]
Taylor, Richard J. K. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON | 2010年 / 66卷 / 33期
基金：
英国工程与自然科学研究理事会;
关键词：
Heck; Horner-Wadsworth-Emmons; Phosphonates; Palladium catalysis; Oxindoles; Tandem reactions; Semaxanib; GW441756; INTRAMOLECULAR HECK REACTION; PALLADIUM-CATALYZED CYCLIZATION; C-H FUNCTIONALIZATION; 3-SUBSTITUTED INDOLIN-2-ONES; KINASE INHIBITORS; OXINDOLE; DISCOVERY; CYCLOADDITION; REARRANGEMENT; CONSTRUCTION;
D O I：
10.1016/j.tet.2010.03.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：6606 / 6612
页数：7
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