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

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-2H-pyran-...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 46; no. 7; pp. 909 - 916
Main Authors Juranovic, Amadej, Kranjc, Kristof, Polanc, Slovenko, Kocevar, Marijan
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
heterogeneous catalysis
ONE-POT SYNTHESIS
MICROWAVE
OF-THE-ART
cycloaddition
boscalid derivatives
biaryls
ASSISTED CATALYTIC TRANSFORMATIONS
heterocycles
ACTIVATED CARBON
CONVENTIONAL REACTION CONDITIONS
2012 PART
DIELS-ALDER REACTION
RESISTANCE
dehydrogenation
SYNTHETIC EQUIVALENT
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Summary: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-2H-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