Abstract
Reaction of diorganozinc reagents with N-(oxopyrrolin-4-yl)-3-chloromethylbenzonitriles provides 5-substituted aminopyrrolo[3,4-b]quinolines by an overall single-pot, tandem alkylation/cyclization sequence. Mechanistic considerations suggest an in situ–generated ortho-quinone methide imine (aza-ortho-xylylene) as a reactive intermediate, which may trap an alkyl group from the diorganozinc reagent by a conjugate addition.
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