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Azomethine ylides from the reaction of 4-(dicyanomethylene)-3-methyl-1-phenyl-2-pyrazoline-5-one with α-amino acids and their esters

✍ Scribed by Metwally, Saoud A. M. ;Aly, Moustafa F. ;Abd-Alla, Mohamed A. ;Atta, Ferial M. ;Abd-El-Monem, Maisa E.

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 255 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199119910168

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✦ Synopsis

Abstract

4‐(Dicyanomethylene)‐3‐methyl‐1‐phenyl‐2‐pyrazoline‐5‐one (1) readily reacts with α‐amino acids and their esters by Michael addition and subsequent elimination of HCN to the adducts 2a–k. One of these, 2i (obtained from methyl glycinate), adds stereoselectively to N‐phenylmaleimide with loss of the remaining cyano group. It is believed that the endo‐transition state of lower energy leads to the major cycloadduct 5, whereas the exo‐transition state gives 6 as the minor one.

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