TY - JOUR
T1 - Exploiting the Different Nucleophilicity of the Isocyano Group
T2 - A Strategy for the Isocyanide Functionalization
AU - Brunelli, Francesca
AU - Russo, Camilla
AU - Giustiniano, Mariateresa
AU - Tron, Gian Cesare
N1 - Publisher Copyright:
© 2024 American Chemical Society
PY - 2024/4/19
Y1 - 2024/4/19
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85189904581&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c02529
DO - 10.1021/acs.joc.3c02529
M3 - Article
SN - 0022-3263
VL - 89
SP - 5833
EP - 5840
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -