Urea-Promoted Neat Synthesis of Fused Dihydroisoquinolines and Disubstituted Pyridines: A Mechanistic Observation with Molecular-Sensing Studies.

An efficient and short synthesis of fused dihydroisoquinolines, diaryl substituted pyridine derivatives in good to high yields has been established by using an environmentally safe, solvent-metal-oxidant-free tandem approach. In this article, we discuss how the electrocyclic reaction is more pronounced in the solid phase in the presence of urea, whereas the typical aza-Michael addition is more prominent in presence of arylamine in the solution phase for 3-(2-formylcycloalkenyl)acrylic ester derivative substrates. The wide range of substrates and urea-promoted neat synthesis made our approach more significant in medical and also analytical science. Moreover, an isoquinoline alkaloid decumbenine B analogue has been synthesized by using our newly developed neat methodology. We have also investigated the photophysical properties of the synthesized fused dihydroisoquinoline derivatives. One of the synthesized molecules was used as a sensor for the selective detection of toxic picric acid. Therefore, the effective neat synthesis and molecular sensing applications of these compounds made our approach more exciting in the field of heterocyclic chemistry.

Synthesis of Multifused Pyrrolo[1,2-a]quinoline Systems by Tandem Aza-Michael-Aldol Reactions and Their Application to Molecular Sensing Studies.

Herein, we have presented a weak acid-promoted tandem aza-Michael-aldol strategy for the synthesis of diversely fused pyrrolo[1,2-a]quinoline (tricyclic to pentacyclic scaffolds) by the construction of both pyrrole and quinoline ring in one pot. The described protocol fabricated two C-N bonds and one C-C bond in the pyrrole-quinoline rings which have been sequentially formed under transition-metal-free conditions by the extrusion of eco-friendly water molecules. A ketorolac drug analogue has been synthesized following the current protocol, and one of the synthesized tricyclic pyrrolo[1,2-a]quinoline fluorophores has been used to detect highly toxic picric acid via the fluorescence quenching effect.