Double domino Knoevenagel hetero Diels–Alder strategy towards bis-pyrano-1,4-benzoquinones

Abstract

Several bis-pyrano-l,4-benzoquinones have been synthesized by a double domino Knoevenagel hetero Diels–Alder reaction. The synthetic approach is highly efficient allowing the construction of complex polycyclic scaffolds with six new σ-bonds. These reactions performed more efficiently and more rapidly using microwave irradiation. The resulting bis-pyrano-1,4-benzoquinones are the first examples of a double domino Knoevenagel hetero Diels–Alder reaction. Our approach represents a novel contribution to the chemistry of 2,5-dihydroxy-l,4-benzoquinones and the first general method for the synthesis of bis-pyranobenzoquinones.