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Electrochemical synthesis of the vinylogs of N-acyl N,O-acetals and their reactivity

✍ Scribed by D. Fasseur; B. Rigo; P. Cauliez; M. Debacker; D. Couturier


Book ID
104222129
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
213 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis


Vinylogs of N-acyl N,O-acetals are formed in good yields by anodic oxidation, in methanol or water, of S-enaminoesters derived from pyroglutamic acid. These new acetals react easily with nucleophiles or silylated amines. Anodic oxidation of N-acylamino acids was first reported in 1979.l The N-acyl N,O-acetals (1) obtained from that reaction, or from the anodic a-methoxylation of lactams


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## Abstract magnified image Various aldehyde and ketone acylhydrazones are synthesized and, under acylating conditions, cyclized into 3‐acyl‐1,3,4‐oxadiazolines. The scope and limitations of these cyclizations and the possible side reactions (__e.g__. formation of the open‐chain __N,O__‐acylhydraz