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. 2012 Nov 8;8:1901–1908. doi: 10.3762/bjoc.8.220

Table 2.

Pyrimido-β-carbolines based on 9.

graphic file with name Beilstein_J_Org_Chem-08-1901-i001.jpg
Entry Substrate R-CHO Pictet–Spengler products 9, R Yield (%)a tR (min)b
1 2a 4-Cl-C6H4-CHO 9a 4-Cl-C6H4 84 14.92
2 2a 4-OEt-C6H4-CHO 9b 4-OEt-C6H4 82 14.14
3 2a 4-OMe-C6H4-CHO 9c 4-OMe-C6H4 78 13.25
4 2a 4-Br-C6H4-CHO 9d 4-Br-C6H4 85 13.90
5 2a 3,4-diCl-C6H-CHO 9e 3,4-diCl-C6H3 80 14.50
6 2c 4-Br-C6H4-CHO 9f 4-Br-C6H4 72 15.89
7 2c 4-NO2-C6H4-CHO 9g 4-NO2-C6H4-CHO 76 15.82
8 2c 4-OMe-C6H4-CHO 9h 4-OMe-C6H4-CHO 79 13.45
9 2c 3,4-diOMe-C6H3-CHO 9i 3,4-diOMe-C6H3 81 12.95
10 2c 4-Cl-C6H4-CHO 9j 4-Cl-C6H4 86 14.82
11 2c 2-Cl-C6H4-CHO 9k 2-Cl-C6H4 78 14.37

aIsolated yield. bRetention time on HPLC (C18 reversed-phase column; 150 mm × 4.8 mm; 5 µm) with a linear gradient of 0–100% CH3CN in water over 30 min. Flow rate of 1.0 mL/min and UV detection at 220/254 nm.