First TDAE Reactivity Using Benzonitrile Derivatives as Substrates and Its Application to the Synthesis of 3-Substituted Isochroman-1-ones

Omar Khoumeri (1) , Thierry Terme (1) , Patrice Vanelle (1)

1 ICR - Institut de Chimie Radicalaire

The first TDAE-initiated reaction between benzonitrile derivatives as substrates and substituted benzaldehydes to form substituted hydroxyethylbenzonitrile derivatives is reported. The 2-hydroxyethyl benzonitrile derivatives thus formed were good candidates for one-pot lactonization in a mixture of hydrochloric acid and methanol at 70 degrees C over five hours. These reactions furnished the corresponding 3-substituted isochroman-1-one derivatives in good yields.

Domains: Chemical Sciences

Omar Khoumeri, Thierry Terme, Patrice Vanelle. First TDAE Reactivity Using Benzonitrile Derivatives as Substrates and Its Application to the Synthesis of 3-Substituted Isochroman-1-ones. Synthesis: Journal of Synthetic Organic Chemistry, 2018, 50 (13), pp.2617--2623. ⟨10.1055/s-0036-1591570⟩. ⟨hal-02091895⟩