100460-68-2Relevant articles and documents
COPPER(II) IN ORGANIC SYNTHESIS. IV REACTION OF THE COPPER(II) ACETATE COMPLEX OF ISATIN-3-ARYLHYDRAZONES WITH DIMETHYL ACETYLENEDICARBOXYLATE.
Coda, A. Corsico,Desimoni, G.,Pappalardo, M.,Righetti, P. P.,Seneci, P. F.,Tacconi, G.
, p. 2545 - 2556 (2007/10/02)
The copper(II) acetate complex of isatin-3-phenylhydrazone (2a) reacted with dimethyl acetylenedicarboxylate (DMAD) by the competitive pathways:a Cu++ oxidation of the ligand and a cycloaddition.The former reaction gave 3-carbenindolin-2-one (13) which reacted with DMAD in a 1,3-dipolar cycloaddition, to give 3a.This was synthesized by an independent route.The phenyl radical, generated in the same process, was trapped by three DMAD and gave 4a.The cycloaddition gave a spiro adduct 10 which, by electrocyclic ring opening and intramolecular cyclization, allowed isolation of a pyridazinoindole (5a).The reaction was performed on p-chlorophenylhydrazone 1b and the structure of 5b was demonstrated by X-ray analysis.A rationalization of the reactivity was attempted in terms of MO interactions of the reactants.
