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

Xiangshu Xiao, Mark Cushman

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)6496-6498
Number of pages3
JournalJournal of Organic Chemistry
Volume70
Issue number16
DOIs
StatePublished - Aug 5 2005
Externally publishedYes

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Isoquinolines
Topoisomerase I Inhibitors
Schiff Bases
Anhydrides
Cyclization
Condensation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A facile method to transform trans-4-carboxy-3,4-dihydro-3-phenyl-1(2H)- isoquinolones to indeno[1,2-c]isoquinolines. / Xiao, Xiangshu; Cushman, Mark.

In: Journal of Organic Chemistry, Vol. 70, No. 16, 05.08.2005, p. 6496-6498.

Research output: Contribution to journalArticle

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