Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

Abstract

An efficient domino approach has been developed for the synthesis of polyheterocyclic derivatives constituting pyrrole moiety. Lewis acid catalyzed reaction of 2‐substituted‐2‐hydroxy‐indane‐1,3‐diones and 1,4‐benzoxazinone derivatives resulted in the formation of polyheterocyclic compounds under metal‐free and mild conditions in good to excellent yield. The reaction is highly regioselective for C−C and C−N bond construction proceeded via intramolecular [3+2] cycloaddition reaction. The protocol is highly efficient, obviates column chromatography and the products are obtained by simple filtration followed by washing with solvent.

Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones

“…1,2 In addition, it is a key component of marine alkaloids like ningalin and lamillarin. 3 On the other hand, the alkylidene or arylidene indanedione system has enormous synthetic utility and is found in many biologically active compounds possessing anti-inflammatory, antibacterial, β-amyloid inhibitory and anticancer properties and that act as therapeutics for hypertension. 4–6 Similarly, some compounds like indanostatin were found to have potential neuroprotective activity against glutamate toxicity, 7 and fredericamycin 8 acts as an anticancer agent.…”