Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels-Alder Reaction with O-(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives.
A highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels-Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avda. Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
Pedro
P
Martín-Acosta
Instituto de Biotecnología-Instituto de Ciencias Básicas, Universidad Nacional de San Juan , Av. Libertador General San Martín 1109 (O), CP 5400, San Juan, Argentina.
Gabriela
G
Feresin
Instituto de Biotecnología-Instituto de Ciencias Básicas, Universidad Nacional de San Juan , Av. Libertador General San Martín 1109 (O), CP 5400, San Juan, Argentina.
Alejandro
A
Tapia
Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avda. Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
Ana
A
Estévez-Braun