Exploiting the Different Nucleophilicity of the Isocyano Group: A Strategy for the Isocyanide Functionalization.
- Resource Type
- Academic Journal
- Authors
- Brunelli F; Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Largo Donegani 2, 28100 Novara, Italy.; Russo C; Dipartimento di Farmacia, Università degli Studi Federico II, Via D. Montesano 49, 80131 Napoli, Italy.; Giustiniano M; Dipartimento di Farmacia, Università degli Studi Federico II, Via D. Montesano 49, 80131 Napoli, Italy.; Tron GC; Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Largo Donegani 2, 28100 Novara, Italy.
- Source
- Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: PubMed not MEDLINE; MEDLINE
- Subject
- Language
- English
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.