Constructing spirooxindoles from non-oxindole precursors: a one-pot nitro-reduction/double lactamization approach to
Raju Chouhan1, Abhijit Gogoi1, Sajal Kumar Das1
1Department of Chemical Sciences, Tezpur University, Napaam, Tezpur, Assam, India 784028. sajalkd@tezu.ernet.in.
Abstract:
2-(2-Nitrobenzyl)-2-(2-nitrophenyl)malonates, readily prepared by SNAr-arylation of diethyl malonate with o-fluoronitrobenzenes, followed by SN2-alkylatioin of the resulting products with o-nitrobenzyl bromides, undergo a tandem Fe/AcOH-promoted nitro-reduction and double lactamization sequence to afford spiro[indoline-3,3'-quinoline]-2,2'-diones in high overall yields. The method is operationally simple, economical, and has a broad substrate scope. The synthetic practicality of this methodology was illustrated by performing the reaction on a gram scale with the same efficiency.
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