Cycloaddition of Styrenes as Phenylacetylene Substitutes on 2H-Pyran-2-ones and the Consequent Metal-Free Dehydrogenation: Case Study of Boscalid Derivatives

Abstract A novel use of styrenes as synthetic equivalents of phenylacetylenes is presented. To show its applicability, the method was tested for the preparation of a set of derivatives of boscalid, a commercially important fungicide. The strategy incorporates the Diels–Alder reaction of 3-acylamino-...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2014-04, Vol.46 (7), p.909-916
Main Authors: Juranovič, Amadej, Kranjc, Krištof, Polanc, Slovenko, Kočevar, Marijan
Format: Article
Language:English
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract A novel use of styrenes as synthetic equivalents of phenylacetylenes is presented. To show its applicability, the method was tested for the preparation of a set of derivatives of boscalid, a commercially important fungicide. The strategy incorporates the Diels–Alder reaction of 3-acylamino-2 H -pyran-2-ones with styrenes, followed by an efficient dehydrogenation step. The latter can be achieved either by the use of chloranil as the oxidant (under microwave irradiation) or by the application of activated charcoal Darco KB acting as a dehydrogenation catalyst (conventional heating).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1338593