A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes

The synthesis of phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes 4 is accomplished via cyclocondensation of 4-oxo-4H-chromen-3-carbaldehydes 1 with appropriately substituted acetic acids 2 under mild conditions. Further treatment of 4 with alcohol or water led to 5-alkoxy- and 5-hydroxy-2H,5H-pyrano[3,2-c]chromen-2-ones 5 and 6, respectively. Acid and thermal catalysed rearrangement of 4–6 gave 5-hydroxypyrano[2,3-b]chromen-2(10aH)-ones 7 and their subsequent substitution led to 5-alkoxyderivatives 8. Reaction of 4 with amides led to 5-acylamino or 5-phenylsulfonamino substituted 2H,5H-pyrano[3,2-c]chromen-2-ones 9. Reactions were performed under heating or microwave irradiation.