ClCCl.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[O:11].[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=[O:14])[CH3:13].CC1[C:27](C)=[C:26](N)[C:25](C)=[C:24](C)[C:23]=1[NH2:32]>CO>[N:4]1[C:5]([CH:10]=[O:11])=[CH:6][CH:7]=[CH:8][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[C:12]([C:15]1[N:16]=[C:17]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:32]=2)[CH:18]=[CH:19][CH:20]=1)(=[O:14])[CH3:13]
The electrospray (ES) mass spectra were recorded using a micromass Quattra LC mass spectrometer with dichloromethane or methanol as the matrix [Masslynx software. open-access autosampler injection]. The infrared spectra were recorded with Universal ATR sampling accessories on a Perkin Elmer Spectrum One FTIR instrument. 1H and 13C NMR spectra were recorded on a Bruker ARX spectrometer 250/300 MHz at ambient temperature; chemical shifts (ppm) are referred to the residual protic solvent peaks. The reagents 2-pyridinecarboxaldehyde, the 2-acetylpyridine, 2,3,5,6-tetramethyl-benzene-1,4-diamine were purchased from Aldrich Chemical Co. and used without further purification. Formic acid (98%) was purchased from Fisons PLC and used without further purification. The compounds 2,2′-bipyridinyl-6-carbaldehyde [J. Uenishi, T. Tanaka, K. Nishiwaki, S. Wakabayashi, S. Oae and H. Tsukube, J. Org. Chem., 1993, 58, 4382], 6-acetyl-2,2′-bipyridine [J. Uenishi, T. Hiraoka, S. Hata, K. Nishiwaki and O. Yonemitsu, J. Org. Chem., 1998, 63, 2481] were prepared according to the indicated journal articles. All other chemicals were obtained commercially and used without further purification.
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