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Rearrangement of 5‐Substituted 5‐Aminopentadienals
Author(s) -
Fischer Fabian,
Berger Daniel,
Neuenschwander Markus
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980817)37:15<2138::aid-anie2138>3.0.co;2-5
Subject(s) - nucleophile , ring (chemistry) , chemistry , salt (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.