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Synthesis of 1-Substituted Pyrrole-3-carboxaldehydes

1983; Taylor & Francis; Volume: 13; Issue: 9 Linguagem: Inglês

10.1080/00397918308063703

1532-2432

Ali Hamdan, Jan W. F. Wasley,

Chemical Synthesis and Analysis

Abstract The Vilsmeier-Haack formylation is the route most frequently employed for the introduction of a formyl group into the 2 or 3 position of a pyrrole ring.2,3 Factors affecting the extent of substitution in the 2 and 3 positions in N-substituted pyrroles under Vilsmeier-Haack conditions have been investigated and the product distribution appears mainly to be the result of steric interactions.4,5 Although it is relatively simple to introduce a formyl residue into the 2-position of a pyrrole nucleus, considerable molecular manipulation must normally be undertaken to prepare pyrrole-3-carboxaldehydes which do not bear substituents in the 2 and 5 positions of the pyrrole ring.6 An alternative method is the generation of isomeric mixtures of pyrrole-2-carboxaldehyde and pyrrole-3-carboxaldehyde by the acid mediated rearrangement of t h e corresponding pyrrole-2-carboxaldehydes.