Diels - Alder reactions of a range of 1-(alkoxy/alkyl/halogen-substituted phenyl)buta-1,3-dienes with methyl propiolate carried out in a green ethanolic medium under 9 kbar pressure were investigated. The use of high pressure as activating method of the Diels - Alder reactions allows efficient and regioselective generation of a series of cyclohexadienylbenzene cycloadducts that are oxidized to the corresponding biaryls. The alkoxy/alkyl/halogen- substituted biaryls produced are useful precursors for accessing substituted 6H-benzo[c]chromen-6-ones and the cannabinols family. © 2012 American Chemical Society.

High-Pressure-Promoted Diels–Alder Approach to Biaryls: Application to the Synthesis of the Cannabinols Family

MINUTI, Lucio;TEMPERINI, Andrea;BALLERINI, ELEONORA
2012

Abstract

Diels - Alder reactions of a range of 1-(alkoxy/alkyl/halogen-substituted phenyl)buta-1,3-dienes with methyl propiolate carried out in a green ethanolic medium under 9 kbar pressure were investigated. The use of high pressure as activating method of the Diels - Alder reactions allows efficient and regioselective generation of a series of cyclohexadienylbenzene cycloadducts that are oxidized to the corresponding biaryls. The alkoxy/alkyl/halogen- substituted biaryls produced are useful precursors for accessing substituted 6H-benzo[c]chromen-6-ones and the cannabinols family. © 2012 American Chemical Society.
2012
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/11391/999666
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 27
  • ???jsp.display-item.citation.isi??? 24
social impact