Synthesis of novel Tröger's bases analogues. The first ones fluorescent by excited state intramolecular proton transfer (ESIPT)

NMR Spectral Correlations in Some Tröger’s Bases

“…Infrared spectra (KBr, 4000-400 cm −1 ) were recorded on AVATAR-300 Fourier transform spectrophotometer. The NMR spectra are recorded in INSTRUM AV500 NMR spectrometer, operating at 500 MHz for 1 H spectra and 125.46 MHz for 13 C spectra in CDCl 3 solvent using TMS as internal standard. Electron impact (EI) (70 eV) and FAB + mass spectra were recorded using VARIAN 500 mass spectrometer.…”

“…Organic chemists synthesized various kinds of Tröger's base derivatives from C-amino heterocycles [4,5, naphthalimide flurophore[6, rigid C 2 -symmetric crown ether [7], Chiral primary bis-ammonium salts [8], rearrangement of pyrazolines [9] mercaptanes [1], halogenation [10] and N-methyl pyrrole units [11,12]. The mechanism of formation of Tröger's base derivatives were investigated Abella et.al., [13] through AEI Mass spectral data. Chiral recognition by phenomena [14,15] was important for various fields likeracemic mixture resolution, determination of enantiomeric purity of chiral compounds and the selectivity of catalysts.…”

Simulation of the interactions between Tröger bases and DNA

“…The first Tröger base was synthesized in 1887 8 and further received considerable interest due to its V-shaped chiral structure (see Figure 1A). 9,10 Recently, Abella et al 11 carried out some studies on Tröger bases, regarding their photophysical properties as well as regarding the detailed investigation of their mechanism of formation. 12 It was also only recently shown that proflavine/acridine and phenanthroline-containing Tröger bases were able to selectively bind B-DNA in a stereospecific fashion.…”

Synthesis and reactivity of dimethoxy-functionalised Tröger’s base analogues

“…38 Two more highly substituted 2,8-dimethoxy Tr€ oger's base analogues, 7 (converted to the dihydroxy analogue 8 upon treatment with acetic acid and hydrochloric acid, at reflux for 48 h) and 9, have also been reported. 39,18 A 1,7-dimethoxy Tr€ oger's base analogue 10 was prepared in 16% yield from a highly functionalised precursor by heating in DMSO solution at 185e190 C for 9 h. 10 Two related 1,7-dihydroxy analogues 11 and 12 were prepared directly from the corresponding aniline precursors 40 and a 2, 3,8,9-tetramethoxy analogue 13 has also been reported. 41 A 2,8-dihydroxy analogue 4 is briefly discussed in the literature, however experimental details were limited to inclusion of the reagents on an experimental scheme.…”