Synthesis of pyrrolo2,3-dpyridazines and pyrrolo2,3-cpyridines (6-azaindoles). Experimental and theoretical study

A new synthetic route towards 6-azaindoles (pyrrolo[2,3-c]pyridines) and pyrrolo[2,3-d]pyridazines starting from 4-aroyl pyrroles is described. This overall protocol involves: (i) the Vilsmeier-Haack reaction to obtain pyrrolo-2,3-dicarbonyles and (ii) condensation with hydrazines or glycine methyl...

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Published in:Organic & biomolecular chemistry 2024-08, Vol.22 (31), p.6331
Main Authors: Efimov, Ilya V, Sultanova, Yana V, Cicolella, Alessandra, Talarico, Giovanni, Voskressensky, Leonid G
Format: Article
Language:English
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Summary:A new synthetic route towards 6-azaindoles (pyrrolo[2,3-c]pyridines) and pyrrolo[2,3-d]pyridazines starting from 4-aroyl pyrroles is described. This overall protocol involves: (i) the Vilsmeier-Haack reaction to obtain pyrrolo-2,3-dicarbonyles and (ii) condensation with hydrazines or glycine methyl ester. The reaction mechanism between pyrrolo-2,3-dicarbonyl with phenyl hydrazine and glycine methyl ester has been modelled using DFT calculations to prove the formation of one from two possible isomers of condensation.A new synthetic route towards 6-azaindoles (pyrrolo[2,3-c]pyridines) and pyrrolo[2,3-d]pyridazines starting from 4-aroyl pyrroles is described. This overall protocol involves: (i) the Vilsmeier-Haack reaction to obtain pyrrolo-2,3-dicarbonyles and (ii) condensation with hydrazines or glycine methyl ester. The reaction mechanism between pyrrolo-2,3-dicarbonyl with phenyl hydrazine and glycine methyl ester has been modelled using DFT calculations to prove the formation of one from two possible isomers of condensation.
ISSN:1477-0539
1477-0539
DOI:10.1039/d4ob00717d