Strategies and Synthetic Methods Directed Toward the Preparation of Libraries of Substituted Isoquinolines

Emelia Awuah and Alfredo Capretta*

*Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada, L8S 4M1, Email: caprettamcmaster.ca

E. Awuah, A. Capretta, J. Org. Chem., 2010, 75, 5627-5634.

DOI: 10.1021/jo100980p

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Abstract

Microwave-assisted Bischler-Napieralski or Pictet-Spengler reactions allowed the production of substituted isoquinoline libraries. The generated dihydroisoquinolines and tetrahydroisoquinolines could be oxidized to their corresponding isoquinoline analogues. A more practical and efficient route to C1- and C4-substituted isoquinolines involves the preparation and activation of isoquinolin-1(2H)-ones.

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Key Words

Tetrahydroisoquinolines, Dihydroisoquinolines, Pictet-Spengler Reaction, Bischler-Napieralski Reaction, Microwave Synthesis

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ID: J42-Y2010-2330