Dihydrofurocoumarin and dihydrofurodihydropyrid-2-one derivatives via palladium catalysed cascades involving aryl/heteroaryl/vinyl iodides and allene followed by acid catalysed cyclisation

被引:18
作者
Grigg, R [1 ]
Nurnabi, M [1 ]
Sarkar, MRA [1 ]
机构
[1] Univ Leeds, Dept Chem, MIDAS Ctr, Leeds LS2 9JT, W Yorkshire, England
关键词
allylpalladium; nucleophiles; allylation; hydroxycoumarins; hydroxyquinolones; pyrones; claisen rearrangement; cyclisation;
D O I
10.1016/j.tet.2004.02.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mono 3-(2'-arylallyl) derivatives of 4-hydroxycoumarin 1a,b, 4-hydroxy-6-methyl-pyran-2-one (3) and 6-hydroxy-1,4-dimethyl-1,2-dihydropyrid-2-one-3-carbonitrile (4) are produced in 3-component cascades involving aryl/heteroaryl/vinyl iodides and allene (1 atm) using Pd(PPh3)(4)/CS2CO3/MeCN/80degreesC or Pd-2(dba)(3)/tris(2-furyl)phosphine/K2CO3/DMF/80degreesC as the catalyst system. 4-Hydroxy-2-quinolone (2) afforded a mixture of mono- and bis-allylation products under these conditions. Mono C-allylation products 5a-e and 15a-e undergo facile acid catalysed cyclisation to afford dihydrofurocoumarins 11a-e and dihydrofurodihydropyrid-2-ones 16a-e in good overall yield. (C) 2004 Elsevier Ltd. All rights reserved.
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页码:3359 / 3373
页数:15
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