Multicomponent Reactions Of Arylglyoxals For The Synthesis Of Functional Materials

Heterocyclic compounds play a very important role in organic,medicinal and materials chemistry.The goal of the current research is to study the multicomponent reactions of arylglyoxals for the synthesis of functional heterocyclic compounds.The first part focuses on a three-component reaction of glyoxals(2-oxoaldehydes),cyclic 1,3-dicarbonyl compounds,and 4-aminopyridines leading to the formation of stable zwitterionic heterocyclic products.The developed procedure is fast,operationally simple and catalyst-free allowing to obtain the target compounds in good to high yields.The second part utilizes arylglyoxals as an aldehyde component in a four-component Ugi reaction to obtain 1,3-dicarbonyl compounds.Their complexation with boron trifluoride diethyl etherate leads to the formation of O,O-chelated boron complexes.The optical properties of these novel luminophores have been studied in THF solution and in solid state,revealing pronounced aggregation-induced emission(AIE)features.Additionally,we have studied the reaction of 2-aminopyridine-3-sulfonyl chlorides with tertiary amines.This reaction proceeds in the absence of any catalyst under the aerobic conditions to give the sulfonylethenamines.The control experiments showed that the 2-aminopyridine-3-sulfonyl chloride plays a dual role in this process promoting the aerobic oxidation of the amine and electrophilically trapping the resulting enamine.These results are discussed in the third part.