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

来源：

TETRAHEDRON | 2004年 / 60卷 / 15期

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.

引用

页码：3359 / 3373

页数：15

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