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Acid-induced dimerization of imidates derived from glycine: Synthesis of methyl N-(1,2,5-trisubstituted-4-imidazoyl)glycinates

✍ Scribed by Florence Morel; Jean Michel Lerestif; Jean Pierre Bazureau; Jack Hamelin; François Tonnard

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
612 KB
Volume
7
Category
Article
ISSN
1042-7163

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✦ Synopsis

A number of N-( I , 2,5-trisubstituted-4-imidazoyl)glycinates 4 were prepared in 60-95% yield from imidates 1 derived from a-amino esters by cyclodimerization without solvent at 70°C in acetic acid medium. According to this process, the reaction of imidate la as a I,3-dipole generated i n situ by thermal 1,2-prototropy with the free ethyl benzimidate as the dipolarophile has been investigated for the first time and gave directly the methyl imidazole-4-carboxylate in moderate yield by regioselective [3 + 21 cycloaddition.

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