Isoindolinone and isobenzofuranone rings are present in a big number of molecules with important biological properties, thus over the past decades a large number of synthetic methods have been developed. However, these methodologies are often complex, nonflexible or require harsh conditions, making the synthetic processes cumbersome. During our studies about the difficult aldol addition of readily enolizable active methylene compounds to aldehydes we developed a series of new methods for the synthesis of 3-substituted heterocyclic compounds, employing electro-initiated, asymmetric organocatalytic and friendly K2CO3 catalyzed approaches. This was allowed thanks to the intramolecular trapping of the unstable aldol adducts intermediates by cyclization at the cyano group of 2-cyanobenzaldehyde and at the ester group of 2-carbomethoxy benzaldehyde. Moreover, further transformations led to a series of interesting highly functionalised molecules, mimicking important biologically active compounds and natural products.
NEW METHODS IN THE SYNTHESIS OF HIGHLY FUNCTIONALIZED ISOINDOLINONES AND ISOBENZOFURANONES
MASSA, Antonio;
2012-01-01
Abstract
Isoindolinone and isobenzofuranone rings are present in a big number of molecules with important biological properties, thus over the past decades a large number of synthetic methods have been developed. However, these methodologies are often complex, nonflexible or require harsh conditions, making the synthetic processes cumbersome. During our studies about the difficult aldol addition of readily enolizable active methylene compounds to aldehydes we developed a series of new methods for the synthesis of 3-substituted heterocyclic compounds, employing electro-initiated, asymmetric organocatalytic and friendly K2CO3 catalyzed approaches. This was allowed thanks to the intramolecular trapping of the unstable aldol adducts intermediates by cyclization at the cyano group of 2-cyanobenzaldehyde and at the ester group of 2-carbomethoxy benzaldehyde. Moreover, further transformations led to a series of interesting highly functionalised molecules, mimicking important biologically active compounds and natural products.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
