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Exploiting the Different Nucleophilicity of the Isocyano Group: A Strategy for the Isocyanide Functionalization
Francesca Brunelli1, Camilla Russo2, Mariateresa Giustiniano2
1Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Largo Donegani 2, 28100 Novara, Italy.
Abstract:
By exploiting the different nucleophilicity of aromatic and aliphatic isocyanides, we selectively react aliphatic isocyano groups while preserving aromatic ones in Passerini and Ugi multicomponent reactions. This simple approach allows the synthesis of α-acyloxy carboxamides or α-acylamino carboxamides possessing one or two isocyanide groups, which are challenging to achieve through traditional formylation and dehydration protocols. These analogues have the potential to serve as valuable building blocks with diverse applications.
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