Tuning Reactivity of Platinum(II) Complexes

O
CH 3
+
I
+
N
O
oH -
N
O O
7
CH 3
Excess
NH 4 OAc
Scheme 3.5: Route used for the synthesis of 4’–(2’’’–CH3–phenyl)–6–(3’’–
isoquinolyl)–2,2’–bipyridine.
A solution of a mixture of 1-(3-isoquinoyl)-3-(o-tolyl)-prop-2-en-1-one (0.892 g, 3.26
mmol), N-{1-(2´-pyridyl)-1-oxo-2-ethyl}pyridinium iodide (1.06 g, 3.26 mmol) and
ammonium acetate (16.2 g, excess) in absolute ethanol (10 ml) was stirred for 1 h under
reflux. The solution was allowed to cool, the resultant precipitate filtered off and washed
with 50% aqueous ethanol. The product was recrystallised from ethanol (95%), after
which it was dried under vacuum, to yield analytically pure off-white needle like
crystals. 4’–(2’’’–CH3–phenyl)–6–(3˝–isoquinoyl)–2,2´–bipyridine: Yield: 34% (0.410
g, 1.10 mmol). 1HNMR (CDCl3); 9.37 (s, 1H), 9.07 (s, 1H), 8.77 (d, 1H), 8.74 (dd, 1H), 8.62
(d, 1H), 8.49 (d, 1H), 8.08 (t, 2H), 7.95 (m, 1H) 7.77 (m, 1H), 7.66 (m, 1H), 7.42 (d, 1H),
7.38 (m, 1H), 7.33 (m, 3H), 2.40 (s, 3H, CH3). LC/MS; [m/z, M + Na] = 396.1476. Anal.
N
CH 3
Calcd: C, 83.6; H, 5.1; N, 11.3; Found: C, 84.1; H, 5.2; N, 11.4%.
N