The first aza Diels-Alder reaction involving an alpha,beta-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter.
The reaction between aromatic imines and methacrolein dimethylhydrazone in the presence of 10% indium trichloride affords in good to excellent yields biologically and synthetically relevant 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C-4 in a one-pot process that involves the formation of two C-C bonds and the stereoselective generation of two stereocenters, one of them quaternary, and this constitutes the first example of an alpha,beta-unsaturated dimethylhydrazone behaving as a dienophile in a hetero Diels-Alder reaction and the first vinylogous aza-Povarov reaction.
Sridharan
Vellaisamy
V
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040, Madrid, Spain.
Perumal
Paramasivan T
PT
Avendaño
Carmen
C
Menéndez
J Carlos
JC
D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000814:Aniline Compounds; D006835:Hydrazones; D011804:Quinolines; C023650:aniline