Abstract
The molecular salt, C23H26N2O2 +·Cl−, was obtained from 1-isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline, which was synthesized by cyclocondensation of α-benzoylamino-γ-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide in the presence of phosphoryl chloride. The tetrahydropyridine ring adopts a twist–boat conformation. In the crystal structure, centrosymmetric dimers are formed by N—H...Cl and C—H...Cl hydrogen bonds.
Highlights
The molecular salt, C23H26N2O2+ÁClÀ, was obtained from 1-isobutyl-8,9dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline, which was synthesized by cyclocondensation of -benzoylamino- -methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide in the presence of phosphoryl chloride
Cyclization of -benzoylamino- -methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide with phosphoryl chloride based on the Bischler–Napieralski reaction results in a heterocyclic compound containing condensed imidazole and isoquinoline rings (Seganish et al, 2012; Iaroshenko et al, 2015; Allin et al, 2005)
Good crystals of the title compound were obtained by slow evaporation of a solution of 1isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline treated with hydrochloric acid
Summary
The relevance of a wide range of potent biological activities of natural and synthetic isoquinoline alkaloids is interesting for the synthesis of new isoquinoline compounds. There are compounds that contain condensed imidazole and isoquinoline rings, for example, cribrostatin 6. Cyclization of -benzoylamino- -methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide with phosphoryl chloride based on the Bischler–Napieralski reaction results in a heterocyclic compound containing condensed imidazole and isoquinoline rings (Seganish et al, 2012; Iaroshenko et al, 2015; Allin et al, 2005). Phosphoryl chloride is used as a reagent and solvent (Fig. 1). From the obtained 1-isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline we could not get suitable single crystals for X-ray diffraction analysis. Good crystals of the title compound were obtained by slow evaporation of a solution of 1isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline treated with hydrochloric acid. The C6, C6A, C10A and C10B atoms of the dihydropyridine ring are almost coplanar (r.m.s. deviation = 0.095 A ).
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