The reaction of coumarin with cyanoacetate derivatives in the presence of a nucleophilic base (alkoxides or piperidine) follows an interesting pathway that involves both a coumarin skeletal rearrangement and a Michael addition, via a coumaric acid derivative, to afford a substituted 4H-chromene skeleton. The particular behavior of this process influences the performance and the type of compounds that can be obtained. We demonstrate that the use of an excess of cyanoacetate affords the 4H-chromene derivative in high yield. An explanation of the mechanism involved in this process is proposed.

Preparation of 2-amino-4H-chromene derivatives from coumarins in basic media

CURINI, Massimo;ROSATI, Ornelio;MARCOTULLIO, Maria Carla;
2006

Abstract

The reaction of coumarin with cyanoacetate derivatives in the presence of a nucleophilic base (alkoxides or piperidine) follows an interesting pathway that involves both a coumarin skeletal rearrangement and a Michael addition, via a coumaric acid derivative, to afford a substituted 4H-chromene skeleton. The particular behavior of this process influences the performance and the type of compounds that can be obtained. We demonstrate that the use of an excess of cyanoacetate affords the 4H-chromene derivative in high yield. An explanation of the mechanism involved in this process is proposed.
2006
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/152227
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 9
social impact