A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and enaminone or 1,2-benzenediamine hydrogen bond donors were synthesized. The enaminone-type catalysts prepared by the transamination N,N-dimethyl enaminones with (9 examples) 1,2-benzenediamine-type in 3 steps from ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evalu...

A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from readily available enaminones and the cyanomethyl sulfonium bromide salt in the presence of cesium carbonate is developed, and a mechanism involving sequential nucleophilic vinylic substitution (S(N)V), intramolecular nucleophilic cyclization and dealkylation reactions is proposed.

A gold(I) catalysed reaction between N-propargylic β-enaminones and arynes was developed to access 3-methylene-1-pyrrolines. The title compounds were obtained in 57-78% yields. This reaction is useful for the generation of substituted 1-pyrrolines exhibiting significant molecular complexity.

A small library of anilino enaminones was analyzed for potential anticonvulsant agents. We examined the effects of three anilino enaminones on neuronal activity of output neurons, mitral cells (MC), in an olfactory bulb brain slice preparation using whole-cell patch-clamp recording. These compounds are known to be effective in attenuating pentylenetetrazol-induced convulsions. Among the three c...

The conditions of the reaction of malononitrile dimer with enaminones and arylidenemalononitrile could be adapted to yield either pyridines or benzene derivatives. A new synthesis of pyrido[1,2-a]pyrimidines from the reaction of malononitrile dimer 1 and 2-phenyl-3-piperidin-1-yl-acrylonitrile (11) is described. Compound 1 condensed with DMFDMA to yield an enaminonitrile that reacted with hydra...

An efficient method has been developed for the synthesis of β-enaminones under solvent-free reaction conditions using PPA-SiO2 as catalyst. The reaction yields were good to excellent (up to 90%). This methodology affords high selectivity and good tolerance of a variety of different functional groups present on both aromatic and aliphatic amines. In addition, the methodology is environmentally b...