Synthesis 2012; 44(14): 2181-2184
DOI: 10.1055/s-0031-1291040
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper(II) Triflate–Sodium Dodecyl Sulfate Catalyzed Preparation of 1,2-Diphenyl-2,3-dihydro-4-pyridones in Aqueous Acidic Medium

Daniela Lanari
a  Laboratory of Green Synthetic Organic Chemistry, CEMIN – Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8, 06123 Perugia, Italy, Fax: +39(075)5855560   Email: luigi@unipg.it   Email: pizzo@unipg.it
b  Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, 06123 Perugia, Italy
,
Oriana Piermatti
a  Laboratory of Green Synthetic Organic Chemistry, CEMIN – Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8, 06123 Perugia, Italy, Fax: +39(075)5855560   Email: luigi@unipg.it   Email: pizzo@unipg.it
,
Ferdinando Pizzo*
a  Laboratory of Green Synthetic Organic Chemistry, CEMIN – Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8, 06123 Perugia, Italy, Fax: +39(075)5855560   Email: luigi@unipg.it   Email: pizzo@unipg.it
,
Luigi Vaccaro*
a  Laboratory of Green Synthetic Organic Chemistry, CEMIN – Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8, 06123 Perugia, Italy, Fax: +39(075)5855560   Email: luigi@unipg.it   Email: pizzo@unipg.it
› Author Affiliations
Further Information

Publication History

Received: 19 March 2012

Accepted: 22 March 2012

Publication Date:
25 May 2012 (eFirst)

Abstract

The reactions between N-benzylideneanilines and ­Danishefsky’s diene proceed smoothly in acidic aqueous medium in the presence of a catalytic amount of copper(II) triflate–sodium dodecyl sulfate [Cu(OTf)2–SDS] to afford the corresponding 1,2-diphenyl-2,3-dihydro-4-pyridones in excellent yields of 84–95%. The aqueous solution containing the catalyst is recovered and reused without any loss in efficiency.

 
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