Double domino Knoevenagel hetero Diels-Alder strategy towards bis-pyrano-1,4-benzoquinones |
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Authors: | Sandra Jimé nez-Alonso,Ana Esté vez-Braun,Á ngel G. Ravelo,Rafael Zá rate,Matí as Ló pez |
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Affiliation: | a Instituto Universitario de Bio-Orgánica ‘Antonio González’, Universidad de La Laguna, Avda. Astrofisico Francisco Sánchez N° 2, 38206, Spain b Instituto Canario de Investigación del Cáncer (ICIC), Hospital Universitario de La Candelaria, 38010 Tenerife, Spain |
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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. |
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Keywords: | Domino reactions Cycloaddition Privileged structures Multicomponent reaction Quinones |
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