Solvent-dependent oxidations of 5-and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Z Mahiout, T Lomberget, S Goncalves…

Index: Mahiout, Zahia; Lomberget, Thierry; Goncalves, Sylvie; Barret, Roland Organic and Biomolecular Chemistry, 2008 , vol. 6, # 8 p. 1364 - 1376

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Citation Number: 5

Abstract

A regioselective synthesis of 4, 7-dimethoxy 5-and 6-azaindoles 2 has been achieved, based on the appropriate choice of ortho-directing or ortho-repulsing groups in the formylation of a pyridine ring. Studies on the regioselectivity of the formylation step and on the preparation of azidoacrylate intermediates 4 are described in this paper. The reactivity of the 5-and 6-azaindole structures towards BBr3-mediated selective monodemethylation ...