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Highly diastereoselective synthesis of spiro[cyclopropane-1,3′-indolin]-2′-ones via catalyst-free cyclopropanation using ethyl diazoacetate
Authors:Ram Awatar Maurya  Chada Narsimha Reddy  Geeta Sai Mani  Jeevak Sopanrao Kapure  Praveen Reddy Adiyala  Jagadeesh Babu Nanubolu  Kiran Kumar Singarapu  Ahmed Kamal
Affiliation:1. Division of Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, AP, India;2. Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India;3. Centre for Nuclear Magnetic Resonance, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
Abstract:
Substituted 3-methyleneindolin-2-ones were efficiently cyclopropanated with ethyl diazoacetate to yield spiro[cyclopropane-1,3′-indolin]-2′-ones in a catalyst-free and highly diastereoselective reaction in a mixture of ethanol–acetonitrile (1:1 v/v) as solvent.
Keywords:Spiro compounds   Ethyl diazoacetate   Cyclopropanation   Stereoselective synthesis   Indolin-2-one
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