ChemInform Abstract: One‐Pot Ring‐Closing Metathesis/1,3‐Dipolar Cycloaddition Through Assisted Tandem Ruthenium Catalysis: Synthesis of a Dye with Isoindolo[2,1‐a]quinoline Structure.

Abstract

Structure. -This reaction yields chromophoric isoindolo[2,1-α]quinoline derivatives with the color depending on the substituents. -(ARISAWA*, M.; FUJII, Y.; KATO, H.; FUKUDA, H.; MATSUMOTO, T.; ITO, M.; ABE, H.; ITO, Y.; SHUTO, S.; Angew. Chem., Int. Ed. 52 (2013) 3, 1003-1007, http://dx.doi.org/10.1002/anie.201206765 ; Fac. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan; Eng.) -Roessler 22-172

Metal-Free Nitrogen-Containing Polyheterocyclic Near-Infrared (NIR) Absorption Dyes: Synthesis, Absorption Properties, and Theoretical Calculation of Substituted 5-Methylisoindolo[2,1-a]quinolines

“…Scheme 2. This Work: Synthesis, Absorbance Properties, and Theoretical Calculation of In addition, we calculated all the above compounds 3a, 3d− h, 3j, 3l, 3m, and 3p (Figure 7) 13 in order to understand a structure and an absorption−wavelength relationships using time-dependent density functional theory (TD-DFT). All calculations were performed using Gaussian 09 (Rev.…”

“…1 H NMR were recorded at 300, 400, and 500 MHz. 13 C NMR spectra were recorded at 101 and 126 MHz. Chemical shifts are given in ppm relative to tetramethylsilane (TMS) and the coupling constants J are given in Hz.…”

“…The spectra were recorded in CDCl 3 as the solvent at room temperature unless otherwise noted. TMS served as the internal standard (δ = 0 ppm) for 1 H NMR and CDCl 3 was used as the internal standard (δ = 77.0 ppm) for 13 (matrix-assisted laser desorption/ionization)-TOF(time-offlight) spectrometer unless otherwise noted. 3a, 3b, and 3c are known compounds.…”

“…In our search for a novel and efficient ruthenium-catalyzed one-pot reaction involving both metathesis and nonmetathesis reactions, 11,12 we previously developed a one-pot ring-closing metathesis (RCM)/oxidation/1,3-dipolar cycloaddition protocol to prepare various isoindolo[2,1-a]quinolines 3 from Nallyl-2-alkenylaniline derivatives 1 (Scheme 1). 13 The key intermediate in this reaction is likely to be azomethine ylide I derived from 1,2-dihydroquinoline 2.…”

“…14 For instance,5,11dioxoisoindolo[2,quinolines are analogs of berberine alkaloids that have been shown to have an inhibitory effect against N 2 -induced hypoxia 14a and inhibit human topoisomerase II. 14b Meanwhile, 7,10-dioxoisoindolo[2,1-a]quinolines, first synthesized by our group, 13 are functional dyes. In particular, we found that compound 3 showed a variety of colors when exchanging the R 1 substituent (R 1 = Ph, Me), including blue, yellow, and red (Scheme 1 and Figure 3), despite the core structure of 3 being the same as that of the 7,10-dioxoisoindolo[2,1-a]quinoline system.…”