Tetrahedron Letters

Direct β-amination reaction in porphyrin systems—a simple route to compounds containing two nitrogen substituents at both β-positions of the same pyrrole unit

S Ostrowski, S Grzyb

Index: Ostrowski, Stanislaw; Grzyb, Sebastian Tetrahedron Letters, 2012 , vol. 53, # 47 p. 6355 - 6357

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Citation Number: 8

Abstract

The direct β-amination of porphyrin derivatives is described. 2-Nitro-meso- tetraarylporphyrins (zinc and copper complexes) react with N, N, N-trimethylhydrazinium iodide (TMHI) in the presence of a base (KOH/DMSO system, ca 70–80° C) to give products of nucleophilic aromatic substitution of hydrogen. In this process, the nucleophilic replacement of a H-atom by an NH2 group takes place. The products obtained, bearing ...