New approach for preparation of 2,3,7-trisubstituted 3,4-dihydroisoquinolinone libraries on solid phase.
In an attempt to prepare 7-substituted 3,4-dihydroisoquinolinone family of compounds, we observed an unexpected decarboxylation. The reaction of 4-nitrohomophthalic anhydride with a Schiff base formed on solid support leads to the formation of core structure. LC-MS and 1H NMR analysis confirmed the structure of unexpected intermediate. A library of 38,400 compounds was produced using this new synthetic approach.
Trega Biosciences, Inc., 9880 Campus Point Drive, San Diego, CA 921214, USA.
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Ni
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Krchnak
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Lebl
D000812:Anhydrides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002853:Chromatography, Liquid; D008401:Gas Chromatography-Mass Spectrometry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D019151:Peptide Library
D000812:Anhydrides; D002264:Carboxylic Acids; D007546:Isoquinolines; D019151:Peptide Library