Issue 29, 2008
From the journal:

Chemical Communications

Double decarboxylative Claisen rearrangement reactions: microwave-assisted de novo synthesis of pyridines†

Donald Craig,*a   Federica Painaa  and  Stephen C. Smithb  

* Corresponding authors

a Department of Chemistry, Imperial College London, South Kensington Campus, London, UK
E-mail: d.craig@imperial.ac.uk
Fax: +44 (0)20 7594 5868
Tel: +44 (0)20 7594 5771

b Syngenta, Crop Protection Research Chemistry, Jealott’s Hill International Research Centre, Bracknell, Berkshire, UK

Abstract

Microwave-assisted double decarboxylative Claisen rearrangement of bis(allyl) 2-tosylmalonates provides substituted 1,6-heptadienes, which may be alkylated, and then converted into pyridines by ozonolysis followed by reaction with ammonia generated in situ under microwave conditions.

Graphical abstract: Double decarboxylative Claisen rearrangement reactions: microwave-assisted de novo synthesis of pyridines

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Article information

DOI
https://doi.org/10.1039/B805078C
Article type
Communication
Submitted
26 Mar 2008
Accepted
15 Apr 2008
First published
14 May 2008

Chem. Commun., 2008, 3408-3410

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Double decarboxylative Claisen rearrangement reactions: microwave-assisted de novo synthesis of pyridines

D. Craig, F. Paina and S. C. Smith, Chem. Commun., 2008, 3408 DOI: 10.1039/B805078C

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