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Vinamidines and Vinamidinium Salts—Examples of Stabilized Push‐Pull Alkenes
Author(s) -
Lloyd Douglas,
McNab Hamish
Publication year - 1976
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197604591
Subject(s) - chemistry , nucleophile , electrophile , reactivity (psychology) , ring (chemistry) , organic chemistry , character (mathematics) , medicinal chemistry , combinatorial chemistry , catalysis , mathematics , medicine , alternative medicine , pathology , geometry
The name vinamidines has been proposed for 1,5‐diazapentadienes: these compounds can be regarded as vinylogous amidines and at the same time as push‐pull substituted (and thereby stabilized) alkenes. Vinamidine and vinamidinium structural elements may also form part of a ring system. Characteristic of this class of compounds are their reactivity toward electrophiles (at C β ) and nucleophiles (C α ) and their regenerative character, i.e. their tendency to undergo substitution instead of addition reactions. Reactions of vinamidinium salts with nucleophiles are of special preparative value: they lead e.g. to pyrazoles, oxazoles, pyrimidines, diazepines, quinolines, and quinolizines.