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Updated: May 11, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
DDQ-mediated direct intramolecular-dehydrogenative-coupling (IDC): expeditious approach to the tetracyclic core of
Subhajit Bhunia1, Santanu Ghosh, Dhananjay Dey
1Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, MP - 462 023, India.
Abstract:
An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of β-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.
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