Solvent-free reaction on KF-alumina under microwave: serendipitous one-pot domino synthesis of new isobenzofuran-1(3H)-ones from alpha-hydroxyketones

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

“…Villemin benzannulation route consists of the reaction of α-hydroxyketones 485 with 2 equiv of tert -butyl 3-oxobutanoate ( 486 ) in the presence of a heterogeneous catalyst KF–Al 2 O 3 under microwave irradiation to produce highly functionalized phthalides 488 in moderate to good yields (Scheme ). Mechanistically, a double Knoevenagel condensation of 485 with 486 furnished the intermediate 487 , which after Claisen–Dieckmann reaction and subsequent aromatization yielded 488 .…”

An Efficient and Facile Synthesis of 5‐Amino‐3‐methyl‐7‐aryl‐1,3‐dihydroisobenzofuran‐4,6‐dicarbonitrile Derivatives Under Mild Conditions

“…The organic base‐catalyzed intramolecular cyclization reaction of o‐alkynylbenzoic acid leading to the 5‐exo selective formation of phthalides in good to excellent yields has been reported by Terada . Functionalized isobenzofuran‐1(3 H )‐ones were prepared by a one‐pot cascade reaction of a‐hydroxyketones with acetylacetonates under microwave . In 2006, Takai reported to synthesize isobenzofuran derivatives from rhenium‐catalyzed insertion of aldehyde into a C‐H bond .…”

Microwave-Assisted Domino Reaction in Organic Synthesis

“…17) (Victoria Gomez et al, 2009). The reaction of α-hydroxyketones with a double equivalent of t-butyl acetylacetonate in the presence of KF-alumina under microwave irradiation afforded isobenzofuran-1(3H)-ones 24 in moderate yield (42%-53%) (Villemin et al, 2006). This work involving one-pot threecomponent cascade process is significant, although only four products were synthesized (Eq.…”