Preparation of pyridopyrazines through tandem Pd-catalyzed C-N/C-C coupling reactions of Ugi adducts.

A Pd-catalyzed selective tandem cyclization of the Ugi adduct via Buchwald-Hartwig/C-H bond functionalization reactions has been reported. This sequence offers an interesting approach for synthesizing a wide range of pyrido[1,2-a]pyrazine-3,6-dione scaffolds under mild reaction conditions in moderate to excellent yields. The scope and limitations of the protocol are discussed.

Highly regioselective and diastereoselective synthesis of novel pyrazinoindolones via a base-mediated Ugi-N-alkylation sequence.

An efficient base-mediated/metal-free approach has been developed for the synthesis of 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-3-carboxamide derivatives via intramolecular indole N-H alkylation of novel bis-amide Ugi-adducts. In this protocol the Ugi reaction of (E)-cinnamaldehyde derivatives, 2-chloroaniline, indole-2-carboxylic acid and different isocyanides was designed for the preparation of bis-amides. The main highlight of this study is the practical and highly regioselective preparation of new polycyclic functionalized pyrazino derivatives. This system is facilitated by Na2CO3 mediation in DMSO and 100 °C conditions.

Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides.

A facile and efficient procedure for the synthesis of substituted thiazole-2(3H)-thiones and thiazolidine-2-thiones by the reaction of primary amines, carbon disulfide, and nitroepoxides is described. By using secondary amines in this protocol, the corresponding dithiocarbamate-substituted phenyl-2-propanones were prepared in excellent yields. In addition, substituted thiazoles and 1-(alkylthio)-1-phenylpropan-2-ones were prepared in reactions of S-alkyl dithiocarbamates and nitroepoxides.