Metal- and base-free spirocyclization of alkylidene oxindoles via photo- and mechanochemically-generated nitrile ylides and nitrile imines as 1,3-dipoles

2025/01/01 by Shweta Singh, Roopam Pandey, Varun Christopher +3 · 1 voice
Chemistry · #Advanced Synthetic Organic Chemistry #Phosphorus compounds and reactions #Synthesis of β-Lactam Compounds

paper · pdf · doi:10.1039/d5qo00851d

openalex publication_date 2025/01/01 · openalex created_date 2025/07/15 · openalex updated_date 2026/07/16

Abstract

We report an efficient, metal- and base-free synthesis of spiro[pyrrolidine-3,3′-oxindoles] and spiro[indoline-3,3′-pyrazol]-2-ones via 3 + 2 cycloadditions of in situ generated nitrile ylides and nitrile imines with alkylidene oxindoles.

Discussions

• ✨ New paper: Metal- & base-free spirocyclization of alkylidene oxindoles via photo- & mechanochemically generated 1,3-dipoles. ⚡ Efficient 3+2 cycloadditions ⚡ Access to spiro[pyrrolidine-oxindoles] [bsky, 0 points, 0 comments]

Related

• Synthesis of Spiro Polycyclic N-Heterocycles and Indolecarbazoles via Merging Oxidative Coupling and Cascade Palladium-Catalyzed Intramolecular Oxidative Cyclization
• Asymmetric [4 + 3] cycloaddition of hydroxyphenyl indolinones to synthesize novel spirooxindoles
• Synthesis of chiral spiro-heterocyclic azides via asymmetric [4 + 2]-cycloaddition of conjugated vinyl azides
• Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products
• Interrupted intramolecular [3 + 2] to 5- endo-dig cyclization: [3 + 2] cycloaddition of nitrile ylides of diazo esters: photo-induced solvent-free gem -diamination to synthesize α-amino-α-substituted α-amino esters