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Heilmittelchemische Studien In Der Heterocyclischen Reihe 36. Mitteilung. Über Sydnonimine. II. Herstellung und Eigenschaften von Sydnoniminen mit Acyl‐, Carbamoyl‐ und Thiocarbamoyl‐Substituenten am exocyclischen Stickstoffatom
Author(s) -
Daeniker H. U.,
Druey J.
Publication year - 1962
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19620450714
Subject(s) - chemistry , nitrogen atom , electrophile , electrophilic substitution , catalysis , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry , group (periodic table)
The preparation of a number of sydnonimines substituted on the exocyclic nitrogen atom by acyl, carbamoyl and thiocarbamoyl is described. Unexpectedly, all these derivatives are bases and form salts with acids. The physico‐chemical properties of these compounds have been studied, especially in view of their basic properties. The chemical behaviour towards acids, bases and catalytic hydrogenation has been investigated. An interesting rearrangement of N‐acyl‐sydnonimines into 1,2,3‐triazoles has been discovered. Finally, some electrophilic substitution reactions and the results of quaternisation experiments are reported.