High yield room temperature synthesis of pyranochromenes in neutral cetyltrimethylammonium bromide micellar media

Pyrano3,2-c]chromene derivatives are heterocycles with a wide range of biological properties. There is actually a need for safer synthesis of heterocycles, using for instance water as a solvent. High selectivity can also be achieved by addition of surface-active reagents to form micelles. Indeed, it is presumed that water facilitates organic reactions by the hydrophobic effect, enhanced hydrogen bonding in the transition state and cohesive energy density. Here, a simple aqueous-mediated protocol is developed for the quantitative synthesis of medicinally relevant pyrano3,2-c]chromene derivatives by the tandem reaction of readily available reagents in cetyltrimethylammonium bromide micellar media. This new method is a modification of the three-component reaction involving Knoevenagel condensation, Michael addition and cyclization reaction. Yields of 3, 4-dihydropyranoc]chromenes ranged from 85 to 99 % at room temperature.