Copper-mediated imine-nitrile coupling leading to unsymmetric 1,3,5-triazapentadienato complexes containing the incorporated iminoisoindolin-1-one moiety.
The copper(II)-mediated integration between various 3-iminoisoindolin-1-ones and neat organonitriles (which play a dual role of solvent and reactant), under heating for ca. 12 h, and without requiring any base, accomplishes the release of the solid (1,3,5-triazapentadienato)Cu(II) complexes [Cu{HN=C(R)N=C(C(6)R(1)R(2)R(3)R(4)CO)N}(2)] (1-11) bearing the incorporated iminoisoindolin-1-one fragment. These compounds were isolated in moderate to good yields (44-78%) and do not require further purification. The iminoisoindolinone-nitrile coupling is Cu(II)-mediated and has a general character insofar as it can be efficiently applied for both unsubstituted (R(1)-R(4) = H) and substituted iminoisoindolin-1-ones (R(1), R(3), R(4) = H, R(2) = Me; R(1), R(4) = H, R(2), R(3) = Cl; R(1)-R(4) = F), and a wide range of nitriles (R = Me, Et, Pr(n), Pr(i), C(6)H(11), CH(2)Ph). Complexes 1-11 were characterized by elemental analyses (C, H, N), FAB(+)-MS, IR spectroscopy, and additionally compounds 1, 2 and 4 by single-crystal X-ray diffraction.
Kopylovich
Maximilian N
MN
Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, TU Lisbon, Av. Rovisco Pais, Lisbon, Portugal.
Luzyanin
Konstantin V
KV
Haukka
Matti
M
Pombeiro
Armando J L
AJ
Kukushkin
Vadim Yu
VY