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Unusual Acid-Catalyzed Rearrangement of Two α,α′-Diimino-oximes

✍ Scribed by Walter Fuhrer; Vittorio Rasetti; Grety Rihs

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
478 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

2‐[2‐(Alkylimino)‐2‐phenylethylidene]pyrrolidines (vinamidines, 3–6) were obtained either via activation of the corresponding vinologous amide 1 with Meerwein salt and subsequent treatment of the intermediate 2 with an amine, or more directly by acid‐catalyzed condensation of the Schiff bases derived from acetophenone with 2‐ethoxy‐1‐pyrroline. Nitrosation of these vinamidines led to α,α′‐diimino‐oximes. In two cases (10, 11), these oximes underwent acid‐catalyzed rearrangement with formation of a 5,6,7,8‐tetrahydroimidazo[1,2‐a]pyridine ring system (12, 13). X‐Ray analysis of one of these products (13) and also of one of the vinamidine salts (6) are presented.

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