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A Facile method to transform trans-4-carboxy-3,4-dihydro-3-phenyl- 1(2H)-isoquinolones to indeno[1,2-c]isoquinolines.

ABSTRACT: The indeno[1,2-c]isoquinolines are an important class of topoisomerase I inhibitors with anticancer activity. The condensation of Schiff bases with homophthalic anhydrides provides a mixture of cis- and trans-4-carboxy-3,4-dihydro-3-phenyl-1(2H)isoquinolones. Although the cis products can be readily converted to indeno[1,2-c]isoquinolines with thionyl chloride, the trans products do not afford indeno[1,2-c]isoquinolines using this method. The present report describes a route for conversion of the trans diastereomers to indeno[1,2-c]isoquinolines using selenoxide elimination and Friedel-Crafts cyclization chemistry.

SUBMITTER: Xiao X 

PROVIDER: S-EPMC2526351 | biostudies-literature | 2005 Aug

REPOSITORIES: biostudies-literature

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A Facile method to transform trans-4-carboxy-3,4-dihydro-3-phenyl- 1(2H)-isoquinolones to indeno[1,2-c]isoquinolines.

Xiao Xiangshu X   Cushman Mark M  

The Journal of organic chemistry 20050801 16

The indeno[1,2-c]isoquinolines are an important class of topoisomerase I inhibitors with anticancer activity. The condensation of Schiff bases with homophthalic anhydrides provides a mixture of cis- and trans-4-carboxy-3,4-dihydro-3-phenyl-1(2H)isoquinolones. Although the cis products can be readily converted to indeno[1,2-c]isoquinolines with thionyl chloride, the trans products do not afford indeno[1,2-c]isoquinolines using this method. The present report describes a route for conversion of th  ...[more]

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