Tetrahedron

Vilsmeier formylation and glyoxylation reactions of nucleophilic aromatic compounds using pyrophosphoryl chloride

IM Downie, MJ Earle, H Heaney, KF Shuhaibar

Index: Downie, Ian M.; Earle, Martyn J.; Heaney, Harry; Shuhaibar, Khamis F. Tetrahedron, 1993 , vol. 49, # 19 p. 4015 - 4034

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Citation Number: 162

Abstract

Reactions of N, N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy- substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the ...