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Note | Regular issue | Vol 68, No. 3, 2006, pp.531-537
Published online, 21st February, 2006
DOI: 10.3987/COM-05-10642
7-(Imidazolidin-1-ylmethyl)quinolin-8-ol: An Unexpected Product from a Mannich-Type Reaction in Basic Medium

Augusto Rivera,* Jaime Ríos-Motta, and Miguel Angel Navarro

*Departamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Carrera 30 # 45-03, Bogotá, Colombia

Abstract

7-(Imidazolidin-1-ylmethyl)quinoline-8-ol, an N-substituted imidazolidine, was synthesized in a one-step reaction between 1,3,6,8-tetraazatricyclo[4.4.1.1]dodecane (TATD) and 8-hydroxyquinoline. Obtaining this substance enhanced the scope of possibilities in the synthesis of unsymmetrically N,N-disubstituted imidazolidines. 1H-NMR spectral studies revealed that this type of substance does not undergo ring-chain tautomerism.