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. Author manuscript; available in PMC: 2013 Apr 2.
Published in final edited form as: Org Biomol Chem. 2010 Jul 29;8(19):4281–4288. doi: 10.1039/c0ob00025f

Scheme 2.

Scheme 2

(a) H2 (1 atm.), Pd/C (3.5 mol%), EtOAc, rt, 24 h (76%); (b) SOCl2, reflux, 2 h (73%); (c) sodium (ethoxycarbonyl)amide, DMF, rt, 1 h (14%); (d) BuNH2, MeOH, rt, 1 h (91%); (e) 3,4-dichlorobenzaldehyde, piperidinium acetate (cat.), DMF, rt, 48 h (47%); (f) acrylonitrile, DABCO, dioxane–water (1 : 1), rt, 24 h (68%); (g) PBr3, Et2O, rt, 2 h (69%); (h) NH3, MeOH, rt, 2 h (12: 19%; 13: 65%); (i) EtOCOCl, Et3N, THF, rt, 1 h (64%).