The 25th ISHC Congress–Santa Barbara CA Aug 23-28, 2015

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Title:
Synthesis of Highly Functionalized 4-Aminoquinolines
Abstract: (Your abstract must use Normal style and must fit into the box. Do not enter author details)
A method for the synthesis of highly functionalized 4-aminoquinolines from sulphynamides and amides is presented. The amides are activated by triflic anhydride (Tf2O) and 2-chloropyridine (2-ClPy) and, as Movassaghi et al. have shown, can be used to prepare a wide range of heterocyclic structures.[1] Sulphynamides can be prepared using copper catalysis and alkyl bromides[2] and further derivatized by using Sonogashira chemistry.[3] The main challenge in existing quinoline syntheses is the functionalization at the C-2 and C-3 positions. By combining the Sonogashira approach with the ynamide/amide methodology a wide range of substitutions at C-3 is possible and the C-2 and C-5 to C-8 positions are also accessible. In order to show the broad applicability of the methodology, it was found that the ynamides also readily react with paracyclophane-based amides, creating very interesting planar chiral compounds.

[1] a) M. Movassaghi, M. D. Hill, O. K. Ahmad, JACS 2007, 129, 10096-10097; b) M. Movassaghi, M. D. Hill, Org. Lett. 2008, 10, 3485-3488; c) M. Movassaghi, M. D. Hill, JACS 2006, 128, 14254-14255; d) M. Radi, S. Schenone, M. Botta, Org. Biomol. Chem. 2009, 7, 2841-2847.
[2] Y. Zhang, R. P. Hsung, M. R. Tracey, K. C. M. Kurtz, E. L. Vera, Org. Lett. 2004, 6, 1151-1154
[3] M. R. Tracey, Y. Zhang, M. O. Frederick, J. A. Mulder, R. P. Hsung, Org. Lett. 2004, 6, 2209-2212.