Synthesis of Pyrrolo[2,3-c]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study (original) (raw)
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To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. Materials and methods. All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV254 chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO2) using ethyl acetate. Results. Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl3-catalyzed imino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by 1H nmr and 13C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. Conclusions. An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry.
Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines
Molecules, 2012
Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxyquinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-aryl-6,8dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-aryl-6,8-bis(2-arylethenyl)-4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined.
Tetrahedron Letters, 2006
Isoquinoline reacts with ethyl bromopyruvate in the presence of dialkyl acetylenedicarboxylates or diaryloylacetylenes to produce dialkyl 1-(2-ethoxy-2-oxoacetyl)pyrrolo[2,1-a]isoquinoline-2,3-dicarboxylates or ethyl 2-[2,3-diaryloylpyrrolo[2,1-a]isoquinoline-1-yl]-2-oxoacetates in good yields. Tetrahedron Letters 47 (2006) 6037-6040 3 J HH = 7.2 Hz, CH 3 ), 3.90 (3H, s, OCH 3 ), 3.93 (3H, s, OCH 3 ), 4.36 (2H, q, 3 J HH = 7.2 Hz, OCH 2 ), 7.14 (1H, t, 3 J HH = 7.2 Hz, CH), 7.47 (1H, t, 3 J HH = 7.2 Hz, CH), 8.47 (1H, d, 3 J HH = 7.3 Hz, CH), 9.51 (1H, d, 3 J HH = 7.2 Hz, CH) ppm. 13 C NMR (125.7 MHz, CDCl 3 ): d = 14.0 (CH 3 ), 52.2 (OCH 3 ), 52.7 (OCH 3 ),
A new approach towards the synthesis of pyrrolo[2,1- a]isoquinolines
Tetrahedron Letters, 2010
Reaction of 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline with activated alkynes affords stable tetrahydropyrrolo[2,1-a]isoquinolin-4-ium ylides. Further reactions of ylide 2 gives access to substituted dihydropyrrolo[2,1-a]isoquinolines in good yields.
Journal of Molecular Liquids, 2020
Six new fused isoquinoline based compounds (compounds 5a-c with pyrrolo[2,1-a] isoquinoline structure and compounds 6a-c with imidazo[2,1-a]isoquinoline skeleton) have been synthesized using the [3 + 2] cycloaddition of the several in situ generated cycloimmonium ylides to ethyl propiolate or ethyl cyanoformate. All the synthesized compounds have been investigated in solution by UV-VIS absorption, steady and time-resolved fluorescence methods. The effect of the substituents on the spectral characteristics has been demonstrated. These derivatives displayed an intense emission between 360 and 420 nm. The emission quantum yields (Φ = 0.54-0.64) of pyrroloisoquinoline derivatives in dimethylsulfoxide (DMSO) were significantly higher than those of imidazoquinolines (0.03-0.16). The fluorescence decay of isoquinoline derivatives follows a biexponential law. A noticeable response of these isoquinoline derivatives to sodium hydroxide was observed.