Versatile reactivity of 3-chloro-2-phenyl-isoindole-1-carbaldehyde: hydrolysis and alkylating rearrangement to 1-amino-4-isochromanones

Iaroslav Baglai (1, 2, 3) , Valérie Maraval (1, 2) , Zoia Voitenko (3) , Carine Guyard-Duhayon (1, 2) , Yulian Volovenko (3) , Rémi Chauvin (1, 2)

1 LCC - Laboratoire de chimie de coordination
2 UT3 - Université Toulouse III - Paul Sabatier
3 Taras Shevchenko National University of Kyiv

3-Chloro-2-phenyl-isoindole-1-carbaldehyde has been prepared from N-phenylisoindolinone under Vilsmeier–Hack conditions. This electrophilic isoindole proved to be stable under the basic conditions used in the final treatment (KOH/MeOH), and for weeks under air in the solid state. Nevertheless, the C–Cl bond proved highly sensitive to any treatment with reducing or alkylating agents targeted towards the pendant carbaldehyde group, giving various phthalimide derivatives. This unique reactivity is exploited for the selective synthesis of new aminoisochromanones

Mots clés: Carbaldehydes; Chloroalkenes; Electrophilic reactivity; Isochromanones; Isoindoles

Domaines: Chimie de coordination

Iaroslav Baglai, Valérie Maraval, Zoia Voitenko, Carine Guyard-Duhayon, Yulian Volovenko, et al.. Versatile reactivity of 3-chloro-2-phenyl-isoindole-1-carbaldehyde: hydrolysis and alkylating rearrangement to 1-amino-4-isochromanones. Tetrahedron, 2012, 68 (34), pp.6908-6913. ⟨10.1016/j.tet.2012.06.014⟩. ⟨hal-02908952⟩