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Rearrangement of 5-Substituted 5-Aminopentadienals
Fabian Fischer1, Daniel Berger1, Markus Neuenschwander1
1Departement für Chemie und Biochemie der Universität, Freiestrasse 3, CH-3012 Bern (Switzerland) Fax: (+41) 31-631-3426.
Abstract:
Strong nucleophiles are needed for inducing ring opening 3→4 since the pyrylium salt intermediates 3, formed from 5-X-substituted 5-aminopenta-2,4-dienals 2 upon treatment with acid, are quite unreactive due to "aromatic" stabilization. However, this allows an easy access to a variety of 2-aminopyrylium salts 3 from "push-pull" enynes 1. X=OAc, F, Cl, Br, I, OPh.
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