Preparation of 2- and 4-arylmethyl N-substituted and N,N-disubstituted anilines via a "green", multicomponent reaction.
[reaction: see text] A new, green, regioselective, one-step, multicomponent reaction of an aldehyde possessing a nonenolizable carbonyl function, cyclohex-2-enone (or a derivative thereof), and primary or secondary amines afforded 2-N-substituted arylmethyl anilines or 4-N,N-disubstituted arylmethyl anilines, respectively. Yields and regioselectivities were good. Evidence for a pathway involving imine and iminium intermediates is presented along with examples demonstrating amenability of the process to combinatorial chemistry.
Rosamilia
Anthony E
AE
ARC Special Research Centre for Green Chemistry, Monash University, Clayton, Victoria 3800, Australia.
Scott
Janet L
JL
Strauss
Christopher R
CR