Original synthesis of benzo[f]indole-4,9-dione derivatives using TDAE strategy

Aida R. Nadji-Boukrouche , Sopheak On , Omar Omar Khoumeri (1) , Thierry Terme (1) , Patrice J Vanelle (1)

1 ICR - Institut de Chimie Radicalaire

A new series of 1-methyl-1H-benzo[f]indole-4,9-dione derivatives was prepared via a one-pot 'Sonogashira-Cyclization' reaction with propagylic alcohol in the presence of a palladium catalyst leading to regio-isomers of 2- and 3-(chloromethyl)-1-methyl-1H-benzo[f]indole-4,9-dione after chlorination. The reaction of the 2- and 3-(chloromethyl)-1-methyl-1H-benzo[f]indole-4,9-dione derivatives with various aldehydes and N-sulfonimides in the presence of TDAE under mild conditions led to the corresponding alcohols and N-sulfonamide derivatives in good yield. (C) 2015 Elsevier Ltd. All rights reserved.

Domains: Chemical Sciences

Aida R. Nadji-Boukrouche, Sopheak On, Omar Omar Khoumeri, Thierry Terme, Patrice J Vanelle. Original synthesis of benzo[f]indole-4,9-dione derivatives using TDAE strategy. Tetrahedron Letters, 2015, 56 (17), pp.2272--2275. ⟨10.1016/j.tetlet.2015.03.074⟩. ⟨hal-01460642⟩