(E)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one
نویسندگان
چکیده
The title compound, C(20)H(19)N(3)O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one (alkaloid de-oxy-vasicinone, isolated from Peganum Harmala) with 4-(dimethyl-amino)-benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one part of the mol-ecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzil-idene 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 inter-actions observed between the benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.7555 (19) Å.
منابع مشابه
(E)-3-Propoxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate
The title compound, C(15)H(16)N(2)O(2)·H(2)O, was synthesized via the alkyl-ation of 3-hydroxy-methyl-idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic mol-ecule and the water mol-ecule both lie on a crystallographic mirror plane. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the components i...
متن کاملSynthesis, molecular structure and reactivity of 5-methylidene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolines.
Synthesis of novel 5-methylidene-1,2,3,5-tetrahydro[2,1-b]-quinazoline derivatives 2-4 with potential biological activities mediated by alpha-adrenergic and/or imidazoline receptors was performed by reacting 2-chloro-4,5-dihydroimidazole (1) with the corresponding 2-aminoacetophenones. Compound 2, which incorporates an enamine moiety, underwent a 1,3-dipolar cycloaddition reaction with the appr...
متن کاملDirect access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions
We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused quinazolinone heterocycles in good to excellent yields.
متن کامل6-Nitro-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione
In the two mol-ecules of the asymmetric unit of the title compound, C(12)H(11)N(3)O(4), the seven-membered diazepine ring adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). The five-membered pyrrole ring, which has an envelope conformation, makes dihedral angles of 60.47 (10) and 54.69 (9)° with the benzene ring of the benzodiaze...
متن کاملCrystal structure of 3-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one
In the title compound, C20H16O3, the hydro-pyran ring adopts a distorted half-chair conformation with the methine C atom and the ring O atom displaced by -0.554 (2) and 0.158 (1) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.020 Å). Its mean plane (all atoms) is inclined to the naphthalene ring system at a dihedral angle of 11.67 (1)°. The dihedral angle between ...
متن کامل