Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations?

Organic & Biomolecular Chemistry Pub Date: 2014-12-22 DOI: 10.1039/C4OB02441A

Abstract

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(III)/Co(II) catalysts and the Paal–Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles.

Graphical abstract: Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations
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