In:
Liebigs Annalen der Chemie, Wiley, Vol. 1980, No. 3 ( 1980-03-27), p. 394-402
Abstract:
Self‐condensation of (β‐Alkoxycarbonylalkylidene)ammonium Salts Iminium chlorides or trifluoroacetates of type 2 , formed by protonation of β‐(alkoxycarbonyl)‐enamines 1 , have been proved to undergo condensation to give derivatives of 4‐alkyl‐2‐amino‐6‐hydroxybenzoic acid 6 via elimination of ammonium salt and alcohol. The structures of 6 had been established by spectroscopic data as well as by further reactions. The range of application of this condensation reaction has been studied and the mechanism is discussed. In the primary step presumably a nucleophilic attack on the alkoxycarbonyl group of the iminium salt 2 takes place by the enamine 1 present in the equilibrium. Analogous reactions are also found for homologues of the enamine 1 (e.g. 11, 13 and 17 ) to give the condensation products 12, 14, 15 , and 20 .
Type of Medium:
Online Resource
ISSN:
0170-2041
DOI:
10.1002/jlac.v1980:3
DOI:
10.1002/jlac.198019800307
Language:
English
Publisher:
Wiley
Publication Date:
1980
detail.hit.zdb_id:
162245-6
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