cis/trans-Isochromanones.: DMAP induced cycloaddition of homophthalic anhydride and aldehydes

被引：28

作者：

Bogdanov, MG ^{[1
]}

Palamareva, MD ^{[1
]}

机构：

[1] Univ Sofia, Fac Chem, Sofia 1164, Bulgaria

来源：

TETRAHEDRON | 2004年 / 60卷 / 11期

关键词：

homophthalic anhydride; aldehydes; cycloaddition; DMAP; pyridine; isochroman-4-carboxylic acids;

D O I：

10.1016/j.tet.2004.01.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homophthalic anhydride (1) reacts with wide variety of aromatic aldehydes, in the presence of chloroform and DMAP (N,N-dimethyl-4-amino-pyridine) at room temperature, to give in high yields cis- and trans-1-oxo-isochroman-4-carboxylic acids. Under these conditions, the trans-isomer is predominant and formation of Perkin-type products was not observed in contrast to the reaction carried out in the presence of pyridine. The unexpected trans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid methyl ester (8) was isolated when the reaction between 1 and thiophene-2-carbaldehyde was carried out in pyridine. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2525 / 2530

页数：6

共 12 条

[1]

BOGDANOV M, IN PRESS

[2] STOBBE CONDENSATION WITH DIMETHYL HOMOPHTHALATE .2. [J].