phosphorus oxychloride, 1-methylpiperazine, and iron powder were purchased
from Sigma-Aldrich (St. Louis, MO), while isatin, 5-nitroisatin, and
2-pyridinecarboxaldehyde were purchased from Acros (Geel, Belgium).
All chemicals, as well as the synthesized precursors, were used without
further purification. 2-Amino-5-nitrobenzylamine hydrochloride was
synthesized according to a procedure published elsewhere.46 The free amine was obtained by the dissolution
of the hydrochloride in a minimal amount of water, addition of 4 equiv
of aqueous ammonia, and collection of the formed precipitate by filtration.
Ethanol was dried over molecular sieves (3 Å), and tetrahydrofuran
(THF) was dried by using a standard procedure (Na/benzophenone).47