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Paper | Special issue | Vol 37, No. 3, 1994, pp.1561-1578
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S111
Selective N-Alkylation of (E)-Urocanic Acid

Nancy Lauth-de Vinguerie, Natalia Sergueeva, Monique Damiot, Hiba Mawlawi, Monique Riviere, and Armand Lattes*

*CNRS, Laboratoire IMRCP, Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 04, France

Abstract

Various methods of selective alkylation of the N (t)- and N (Π)- nitrogen atoms of (E)- urocanic acid derivatives are reported. Solid-liquid phase transfer catalysis gave the best results for N (t)-alkylation of urocanic acid alkyl esters. Liquid-liquid phase transfer catalysis allowed direct N (t)-alkylation of urocanic acid itself. The N (Π)-nitrogen atom was alkylated after protection of the N (t)-nitrogen with a phenacyl group.