A Facile method to transform trans-4-carboxy-3,4-dihydro-3-phenyl- 1(2H)-isoquinolones to indeno[1,2-c]isoquinolines.
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.
Xiao
Xiangshu
X
Department of Medicinal Chemistry and Molecular Pharmacology and the Purdue Cancer Center, School of Pharmacy and Pharmaceutical Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
Cushman
Mark
M
D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D007192:Indenes / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D013237:Stereoisomerism; D013461:Sulfur Oxides / Q000737:chemistry
D007192:Indenes; D007546:Isoquinolines; D013461:Sulfur Oxides; C023589:thionyl chloride; D006859:Hydrogen