A novel and highly efficient protocol has been developed for the regioselective synthesis of 2-iminothiazole derivatives with potential biochemical interest by the reaction of enaminones, potassium thiocyanate (KSCN), and N-bromo succinimide (NBS) under mild conditions. The reaction proceeds via the formation of α-bromo enaminones as a versatile intermediate followed by thiocyanation/intramolec...

An oxidative boron-Heck reaction of cyclic enaminones with arylboronic acids is reported. This protocol provides a regioselective arylation at the C6 position of cyclic enaminones. When an N-carbamylated cyclic enaminone was employed, a switch to a conjugate addition reaction occurred in the presence of acid.

Starting from acid chlorides, alkynes, tryptamines, and acryloyl chloride, 21 densely substituted tetrahydro-β-carbolines were prepared in a four-component, one-pot reaction. In this study, the aza-Michael addition step to generate intermediate enaminones was optimized presence of ytterbium triflate. Moreover, apart all reactants could be deployed almost equimolar ratios, which increases atom e...

A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

The fortuitous modification of a quinoline-proline-piperazine side chain linked to a steroid in the presence of lithium (trimethylsilyl) acetylide has generated an unknown product that is more active than its precursor. After having characterized two β-enaminones (two-carbon homologation compounds) that were generated from a simplified model side chain, we have identified the unknown product as...

In present paper a simple procedure for the synthesis of enaminones without catalyst from 1,3-diketones that reacted with primary or secondary amines in ethanol as solvent, as well as the reaction of enaminones with unsaturated esters such as dimethyl acetylene dicarboxylate are reported.