Synthesis of 1,2,3,4-Tetrahydroacridine and 5,6,7,8-Tetrahydroquinoline Derivatives as Potential Acetylcholinesterase Inhibitors

Cobalt(II) chloride-mediated synthesis of beta-enamino compounds under solvent-free conditions

“…β-Enaminones have attracted much attention due to the fact that they are important synthons for the synthesis of many biologically active compounds such as dopamine auto-receptor agonists, 1 acetylcholinestersase inhibitors 2 and anticonvulsants. 3 They are also useful intermediates for the preparation of several aminoacids, 4 aminols, 5 peptides and alkaloids.…”

Domino [3+2] Cycloaddition/Annulation Reactions of β‐(2‐Aminophenyl)‐α,β‐ynones with Nitrile Oxides: Synthesis of Isoxazolo[4,5‐c]quinolines

“…For example, Staskun4a prepared 3‐methyl‐4‐phenylisoxazolo[4,5‐ c ]quinoline by heating 2‐phenyl‐3‐acetyl‐4(1 H )‐quinolone oxime above its melting point (290 °C). Recently, a number of isoxazoloquinolines have been identified as MRP1 inhibitors5 and a new class of isoxazoloacridines and isoxazoloquinolines was prepared as potential acetylcholinesterase inhibitors 6. Despite their importance, the limited synthetic methodologies for their construction may represent the bottleneck for further studies and developments in medicinal chemistry.…”

Ni(OAc)2: a highly efficient catalyst for the synthesis of enaminone and enamino ester derivatives under solvent‐free conditions

“…NMR spectra were performed in CDCl 3 and recorded on a Bruker Avance 300 spectrometer. IR spectra were obtained using a Bruker-Tensor 27 spectrometer.…”

“…However, the azeotropic removal of water is usually required using a Dean-Stark trap in a refluxing aromatic solvent. [12] Several improved procedures have been reported using a variety of catalysts such as trimethylsilyl trifluoromethanesulfonate (TMSTf), [13] montmorillonite K10 under microwave irradiation [14] or ultrasound, [15] I 2 , [16] BF 3 • OEt 2 , [17] Al 2 O 3 , [18] Zn(ClO 4 ) 2 • 6H 2 O, [19] Zn(OAc) 2 • 2H 2 O, [20] [21] ZrOCl 2 • 8H 2 O, [22] NaAuCl 4 , [23] Bi(OTf) 3 , [24] Sc(OTf) 3 , [25] CAN, [26] NaHSO 4 , [27] HClO 4 • SiO 2 , [28] silica gel, [29] natural clays, [30] LProline, [31] silica chloride, [32] silica-supported sulfuric acid, [33] silicasupported antimony(III) chloride, [34] phosphotungstic acid, [35] sulfated zirconia, [36] tin tetrachloride, [37] CAN, [38] K-7 PW 11 CoO 40 , [39] copper(II) nitrate trihydrate [40] and ZrCl 4 . [41] Recently, this condensation reaction has also been performed in water, [24a,42] PEG-water [43] or ionic liquid medium.…”

“…[1] The latter compounds are a highly versatile class of intermediates for the synthesis of heterocycles and pharmaceutical compounds, such as dopamine auto-receptor agonists, [2] acetylcholinestersase inhibitors, oxytocin antagonists [3] and anticonvulsants. [4] Owing to their wide range of activity and importance, many synthetic methods have been developed for the preparation of these compounds.…”