184359-02-2Relevant academic research and scientific papers
Preparation of ortho-hydroxyalkylanilines as ortho-quinone methide imine precursors via an aminoborane complex
Migneault, David,Bernstein, Michael A.,Lau, Cheuk K.
, p. 1506 - 1513 (2007/10/03)
A general process for ortho-specific hydroxyalkylation of secondary anilines has been developed.N-Methylanilinochlorophenylboranes react readily with aryl aldehydes, and with α,β-unsaturated or saturated aliphatic aldehydes to give the corresponding ortho-hydroxyalkylanilines in good yield.Thermolysis of the latter generated the corresponding ortho-quinone methide imine, which can participate in an electrocyclic or intramolecular cycloaddition reaction to give various dihydro- and tetrahydroquinoline derivatives.Application of the method to the syntheses of 5-aza anal ogs of hexahydrocannabinol is demonstrated.Key words: quinone methide imine, ortho-hydroxyalkylaniline, azacannabinoids.
