Abstract
The title compound, C21H14N2O2, was prepared by Pictet-Spengler cyclization of tryptamine and 4-formyl coumarin. In the mol-ecule, the dihedral angle between the mean planes of the coumarin and β-carboline ring systems is 63.8 (2)°. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains along the b-axis direction. Within the chains, there are a number of offset π-π inter-actions present [shortest inter-centroid distance = 3.457 (2) Å].
Highlights
The title compound, C21H14N2O2, was prepared by Pictet–Spengler cyclization of tryptamine and 4-formyl coumarin
Occurring coumarins (Murry, 2002) and their derivatives have a vast number of applications in different areas
Coumarin dyes are widely used in blue–green organic dyes (Schafer, 1990; Duarte & Hillman, 1990; Duarte, 2003) and in OLED emitters (Duarte et al, 2005)
Summary
Occurring coumarins (Murry, 2002) and their derivatives have a vast number of applications in different areas. Norharman is a -carboline alkaloid which has the basic structural unit for a wide range of naturally occurring compounds, and is found in plants, animals and humans (Fekkes et al, 1992). They are used widely as neurotoxins to Parkinson’s disease (Kuhn et al, 1996) and as mediators in the mutagenesis of DNA in the presence of another molecule (Mori et al, 1996). Norharman exhibits a one-dimensional herringbone motif (Thatcher & Douthwaite, 2011) Due to their extensive natural occurrence and common biological origin, there are no reports on compounds which contain these two systems in a single molecule. The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level
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