(<i>E</i>)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro-1<i>H</i>,9<i>H</i>-pyrrolo[2,1-<i>b</i>]quinazolin-9-one
Burkhon ElmuradovS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, UzbekistanR. Ya. OkmanovS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, UzbekistanА. Ш. АбдуразаковS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, UzbekistanB. TashkhodjaevS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, UzbekistanK.M. ShakhidoyatovS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
ABI
Abstract
The title compound, C20H19N3O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one (alkaloid deoxyvasicinone, isolated from Peganum Harmala) with 4-(dimethylamino)benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one part of the molecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzilidene ring (r.m.s. deviation = 0.0080 Å), forming a dihedral angle of 5.0 (1)°. The crystal structure is stabilized by two aromatic π–π stacking interactions observed between the benzene rings of neighboring molecules [centroid–centroid distance = 3.7555 (19) Å.
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