Issue 9, 2007

The first aza Diels–Alder reaction involving an α,β-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter

Abstract

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 α,β-unsaturated dimethylhydrazone behaving as a dienophile in a hetero Diels–Alder reaction and the first vinylogous aza-Povarov reaction.

Graphical abstract: The first aza Diels–Alder reaction involving an α,β-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter

Supplementary files

Article information

Article type
Communication
Submitted
28 Feb 2007
Accepted
26 Mar 2007
First published
04 Apr 2007

Org. Biomol. Chem., 2007,5, 1351-1353

The first aza Diels–Alder reaction involving an α,β-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter

V. Sridharan, P. T. Perumal, C. Avendaño and J. C. Menéndez, Org. Biomol. Chem., 2007, 5, 1351 DOI: 10.1039/B703083E

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