Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane.: New synthesis of benzo[b]xanthones

被引：45

作者：

Sandulache, A ^{[1
]}

Silva, AMS ^{[1
]}

Cavaleiro, JAS ^{[1
]}

机构：

[1] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal

来源：

TETRAHEDRON | 2002年 / 58卷 / 01期

关键词：

Diels-Alder reactions; chromone-3-carboxaldehydes; ortho-benzoquinodimethane; benzo[b]xanthones; oxidation reactions;

D O I：

10.1016/S0040-4020(01)01131-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels-Alder reactions of 12 and 7 followed by the in situ deformylation. The oxidation of adducts 8 and 9 with dimethyl sulfoxide in the presence of iodine gave the novel benzo[b]xanthones 11 in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：105 / 114

页数：10

共 62 条

[21] Reactivity of hindered 1,1-dimethylbutadienes towards α,β-unsaturated enones. [J].