The Use Of Multicomponent Reactions And Post-MCR Transformations For The Synthesis Of Azulene Derivatives And Substituted Morpholines

Due to its unique structure and photophysical properties,azulene derivatives can be widely used in sensors,biological imaging,nonlinear optics(NLO),optoelectronics,molecular electronics,etc.Therefore,advanced organic materials based on azulene have received extensive attention from scientific community in recent years.They have been successfully applied in solar cells and in organic field effect transistors.This has invoked substantial interest in developing new synthetic methods for the construction and functionalization of azulene,especially towards the assembly of azulene fused heterocycles,azulene heterocyclic conjugates and azulene-containing polymers.On the other hand,many multicomponent reactions have been developed to form heterocyclic compounds with diverse structures based on the ability of aryl glyoxal to react with 1,3-dicarbonyl compounds and other nucleophiles.In this work,we attempt to couple this strategy with a nucleophilic potential of a five-membered ring of azulene nucleus to synthesize diverse azulene derivatives.This manuscript mainly consists of the following three parts:The first part describes a series of three-component reactions of azulene,arylglyoxal and 1,3-dicarbonyl compounds towards polyfunctional azulene-containing adducts through the Knoevenagel condensation/Michael addition sequence.This method provides a simple and effective way to synthesize azulene derivatives in a diversity-oriented fashion.The second part introduces the strategy for preparing azulene-tetrahydrocinnolin-5-one conjugates and azulene-dihydroindole-4-one conjugates by the condensation reactions of previously obtained azulene adducts containing 1,4-diketone units with various nitrogen nucleophiles.The reaction has the advantages of mild conditions and simple operation.The third part mainly introduces the method for preparing morpholine compounds bearing different substituents by means of Ugi reaction and subsequent intramolecular umpolung oxa-Michael addition catalyzed by PPh3.This provides a new and straightforward method for synthesizing morpholine compounds from readily available starting materials.