1,3-Diphenylpropane-1,3-diamines, IV. Synthesis of 1,3-Bis(hydroxy-halogenophenyl)propane-1,3-diamines and their Pt(II) Complexes. Part B: Preparation of the Pt(II) Complexes

✍ Scribed by Thomas Kammermeier; Wolfgang Wiegrebe

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 878 KB
• Volume: 327
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19943270904

✦ Synopsis

A: preceeding paper. -As parts A and B are closely correlated to each other, the compounds are numbered consecutively. +) Dedicated to Prof. Dr. S. Ebel, Wiirzburg, on the occasion of his 60th birthday. MeOWconc. ammonia 100/1.5 (v/v).-Solvent II: EtOH 96%/conc. ammonia 100/1.5 (v/v).-The light-grey, non-crystalline complexes melt with decomposition. meso-Dichloro-1 J-bis-(2-methoxyphenyl)propane-1,.3-diamino-Pt(ll) (114)') From 60 x 2 HCI; solvent I; 25%. m.p. 205-208".-C17H22C12N202Pt (552.4) Calcd. C 37.0 H 4.01 N 5.1 Found C 37.4 H 4.09 N 4.8.-FT-IR (KBr): v" = 3258 s, 3189, 3120 m (NH2); 2957 m, 2927 m (C-H aliph.); 2857 m (OCH,); 1603 s, 1595 s (C=C and NH2).-'H-NMR ([D,]DMF): 6 (ppm/250 MHz) = 7.52-6.82 (m; 8H aromat.), 5.53-5.09 (m; 4H, NH2; WD-exch.), 4.70-4.47 (m; 2H, C H HPexch.: 4.59; a x 2 , 'JAX = 1 .O Hz, 'JBX = 1.04 HZ), 3.93 (s; 6H, OCH,), 2.64-2.57 (ABX,; 2Jm = 14.0 Hz. ,JBX = 10.4 Hz, IH, CH2. Ha), 2.30-2.13 (ABX2; 2Jm = 14.0 Hz, 3Jfi = 1.0 Hz. IH, CH2, Hq).-PI-FAB-MS (glyceroVDMS0/194Pt): m/z = 1065.1 ((LzPtzCI3'); 629.2 ((M + H + DMSO)+); 593.3 ((M -C1 + DMSO)+); 515.3 ((M -Cl)+).

Dimers of the type [(L$t2Cl3)+1 were also observed by Sperl') in the PI-FAB-spectra of cis-dichloro-Pt(I1) complexes of estradiol derivatives.

rac-Dichloro-I ,3-bis-(2-methoxyphenyl)propane-1,3-diamino-Pt(ll) (115)

From 61 x 2 HCI; solvent I; 11%. m.p. 209-21 lo.-C17H22C12N202Pt (552.4) Calcd. C 37.0 H 4.01 N 5.1 Found C 36.4 H 3.94 N 5.0.-FT-IR (KBr): v" = 3264 s, 3191 m, 3114 m (NH2); 3017 w (C-H aromat.); 2969 m, 2938 m (C-H aliph.); 2840 m (OCH3); 1601 s, 1589 s (C=C and NH2).-'H-NMR ([DTIDMF): 6 (ppm/250 MHz) = 8.47-6.91 (m; 8H aromat.), 5.66-5.50 (m; 2H. NH2; H/D-exch.), 5.39-5.10 (m; 2H, NH,; H/D-exch.), 4.38-4.17 (m; 2H, CH; W-exch.: 4.27; A2X2, 3JAx = 5.1 Hz), 3.77 (s; 6H, (glycerol/DMSO/"%): m/z = 1064.9 (&Pt2C13)+); 643.1 ((M + H + glycerol)'); 629.1 ((M + H + DMSO)+); 593.2 ((M -C1 + DMSO)+); 551.2 OCHS), 2.38 (A2X2, 3 J ~x = 5.1 Hz, 2H, CH2).-PI-FAB-MS ((M + H)+); 515.2 ((M -CI)+).

meso-Dichloro-I ,3-bis-(3-hydroxyphenyl)propane-l,3-diamino-Pt(ll) (116)

From 88; solvent I; 45%, m.p. 227-23OO.-C,5H,,C12N202Pt (524.3) Calcd. C 34.4 H 3.46 N 5.3 Found C 34.4 H 3.32 N 5.3.-FT-IR (KBr): F =