Selective Tsuji-Trost type C-allylation of hydrazones: a straightforward entry into 4,5-dihydropyrazoles

Elhachemia Elmamouni (1, 2) , M. Cattoen (3) , Marie Cordier (4) , Janine Cossy (5) , Stellios Arseniyadis (5, 3) , Hocine Ilitki (2) , Laurent El Kaim (1)

1 DCSO - Laboratoire de synthèse organique
2 USTO MB - Université des sciences et de la Technologie d'Oran Mohamed Boudiaf [Oran]
3 QMUL - Queen Mary University of London
4 LCM - Laboratoire de chimie moléculaire
5 CBI - Chimie-Biologie-Innovation (UMR 8231)

The 4,5-dihydropyrazole motif has drawn considerable attention over the years as it was shown to exhibit a plethora of biological and pharmacological properties, including anticancer, antibacterial, antifungal, antiviral, and anti-inflammatory properties. As such, it has been the target of a number of methods and drug discovery programs. We report here a straightforward and highly selective approach featuring a key palladium-catalysed Tsuji-Trost type C-allylation and subsequent intramolecular 1,4-addition of hydrazones.

Domains: Chemical Sciences; Organic chemistry

Elhachemia Elmamouni, M. Cattoen, Marie Cordier, Janine Cossy, Stellios Arseniyadis, et al.. Selective Tsuji-Trost type C-allylation of hydrazones: a straightforward entry into 4,5-dihydropyrazoles. Chemical Communications, 2016, 52 (100), pp.14490-14493 ⟨10.1039/c6cc08171a⟩. ⟨hal-01623194⟩