Friedlander-Type Reaction of 4-Cholesten-3-one with 2'-Aminoacetophenone: Angular versus Linear Quinoline-Fused Steroids

To optimize the experimental conditions used for the Friedlander-type condensation, an angular fused 4-substituted quinoline steroid has been obtained in very high yield and regioselectivity using readily available 4-cholesten-3-one and 2'-aminoacetophenone. Moreover, by varying the reaction conditions and the catalyst, the corresponding linear regioisomer was also achieved with an acceptable isolated yield and high chemoselectivity. Both structures have been definitively elucidated via 2D-NMR and fully characterized.

Automated summary

By optimizing the experimental conditions, two compounds with different regioisomers were successfully synthesized with high yield and selectivity. The structures of the synthesized compounds were definitively elucidated through detailed characterization.