Allylic azides as potential building blocks for the synthesis of nitrogenated compounds

Antimicrobial activity of allylic thiocyanates derived from the Morita-Baylis-Hillman reaction

“…In the course of our research interest ( Meier et al , 2012 ; Sá, 2003 ; Sá et al , 2007 ) in the chemistry of Morita-Baylis-Hillman (MBH) adducts ( Basavaiah et al , 2010 ; Basavaiah and Veeraraghavaiah, 2012 ; Singh and Batra, 2008 ) and the antimicrobial activity of synthetic derivatives ( Silveira et al , 2012 ), we have been able to readily install the S-C-N framework through chemical synthesis in aqueous medium under mild conditions to give the corresponding allylic isothiouronium salts or thiocyanates in excellent yields. Herein, we present our results for the screening of a family of allylic thiocyanates against bacteria and fungi strains with a view to developing novel antibiotic agents.…”

Methyl (Z)-2-(bromomethyl)-3-(3,4-methylenedioxyphenyl)prop-2-enoate

“…Multifunctional allylic bromides such as the title compound, (I), are versatile building blocks for the stereoselective construction of natural products and heterocycles of biological relevance (Drewes & Emslie, 1982;Hoffmann & Rabe, 1985;Cheskis et al, 1990;Roush & Brown, 1993;Basavaiah & Hyma, 1996;Grassi et al, 1997;Mateus et al, 2001;Fernandes et al, 2004). Preparation of allylic bromide (I) can be achieved in good yield and excellent stereoselectivity by treating the corresponding -methylene--hydroxy ester (II) (a Baylis-Hillman adduct) (Basavaiah et al, 2003;Ciganek, 1997;Sá , 2003;Hoffmann & Buchholz, 1991) with a combination of HBr and H 2 SO 4 , as previously reported (Fernandes et al, 2004). Careful crystallization from hexane-ethyl acetate (9:1) furnished colourless crystals (m.p.…”