Issue 0, 1986

Stereochemistry of the tetrahydroquinolines from the condensation of methylaniline and glycolaldehyde

Abstract

N-Methylaniline reacts with hydroxyethanal in ethanol at 20 °C to give 3a-hydroxy-2α-hydroxymethyl-1-methyl-4β-(N-methylanilino)-1,2,3,4-tetrahydroquinoline (6), the structure of which has been established by X-ray crystal structure analysis. The heterocyclic ring adopts a C3-sofa conformation in which the methylanilino residue and the hydroxy group are equatorial and the hydroxymethyl group is axial. The dioi (6) readily undergoes thermal or acid-catalysed elimination of methylaniline to give the bridged tetrahydroquinoline (9).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 1151-1155

Stereochemistry of the tetrahydroquinolines from the condensation of methylaniline and glycolaldehyde

A. B. Turner, B. I. McBain, R. A. Howie and P. J. Cox, J. Chem. Soc., Perkin Trans. 1, 1986, 1151 DOI: 10.1039/P19860001151

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements