Conjugated addition of bis(oxazolinyl)zinc to substituted 2-nitrovinyl benzenes: an alternative synthesis of (±)-Rolipram

From Paracetamol to Rolipram and Derivatives: Application of Deacetylation-Diazotation Sequences and Palladium-Catalyzed Matsuda-Heck Reaction

“…Several syntheses of rolipram proceed via addition of nitromethane to an α,β-unsaturated ester or amide 2,[6][7][8] or via addition of an enolate to a nitrostyrene. 9,10 Recently, an enantioselective Pd-catalyzed allylic alkylation of nitromethane has been used, followed by hydroboration-oxidation to establish the required carboxylic acid. 11 In all these cases, lactam formation occurs spontaneously upon reduction of the nitro group.…”

4,4-Dimethyl-2-[3-nitro-2-phenyl-1-(phenylsulfanyl)propyl]-4,5-dihydro-1,3-oxazole

“…While developing a new route aiming at the synthesis of 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one (Rolipram), a phosphodiesterase-4 inhibitor which has been shown to have anti-inflammatory properties (de Visser et al, 2008), the title compound, (I), was obtained during a systematic study of the addition reaction of oxazolines to nitroestyrene (Villar, 2008;Oliveira et al 2007). The crystals were crystallographically characterized and the results are now reported herein.…”

Aplicação de amidetos metálicos na funcionalização de aril-2-oxazolinas de interesse sintético

“…(FRUMP, 1971;GANT;MEYERS, 1994). Esta função também possui muitas outras aplicações como em reações de ativação C-H, como auxiliares quirais em síntese assimétrica (CAPRIATI et al, 2007;GIRI;YU, 2005;OLIVEIRA et al, 2007) e em ciências de materiais (ZENG et al, 2011;CHE et al, 2016).…”