Abstract
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-6 H-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.
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