One‐pot Synthesis of 1,8‐Dioxo‐decahydroacridine Derivatives in Aqueous Media

Abstract

A new and efficient method for the synthesis of 1,8-dioxo-9-aryl-decahydroacridine derivatives was developed via a one-pot three component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of ammonium chloride, or Zn(OAc) 2 •2H 2 O or L-proline separately in water in the short period of time and high yields.

An Efficient One‐Pot Synthesis of 1,8‐Dioxodecahydroacridines Using Silica‐Supported Polyphosphoric Acid (PPA‐SiO2) under Solvent‐Free Conditions

“…The crude product was collected from the filtrate after cooling to room temperature and recrystallized from ethanol to give compounds 3a-l in high yields. All of the 1,8-dioxodecahydroacridine Reaction cycles Yields % derivatives are known and were identified by comparison of their physical and spectroscopic data (IR, NMR) with those of authentic samples 8,16,17,23,24 .…”

Extraordinary catalytic activity of a Keplerate-type giant nanoporous isopolyoxomolybdate in the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxodecahydroacridines

“…1,4-DHPs are also commercially used as calcium channel blockers for the treatment of cardiovascular diseases, including hypertension [34]. Generally, 1,8-dioxo-octahydroxanthenes and 1,8-dioxodecahydroacridines are synthesized by one-pot MCRs in the presence of various catalysts [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52]. Nevertheless, in most of these methodologies, the reaction times are long.…”

One-Pot Synthesis of 1,8-Dioxodecahydroacridines and Polyhydroquinoline using 1,3-Di (bromo or chloro)-5,5-Dimethylhydantoin as a Novel and Green Catalyst under Solvent-Free Conditions

“…However, these methods suffer from drawbacks such as long reaction time, the use of a large quantity of volatile organic solvents, harsh refluxing conditions and lower yields. Thus, chemists have developed several alternative and more efficient methods for the synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives which include the use of microwave irradiation [11], HClO 4 .SiO 2 [12], molecular iodine [13], ionic liquids [14], NH 4 Cl or Zn(OAc) 2 [15], organocatalysts [16], scolecite [17], HY-zeolite [18], p-TSA [19], montmorillonite K10 clay [20] [27], sulfamic acid [28], so- One-Pot Synthesis of 1,8-Dioxodecahydroacridines and Polyhydroquinoline using 1,3-Di (bromo or chloro)-5,5-Dimethylhydantoin 291 lar thermal energy [29], carbon-based solid acid (CBSA) [30], ZnO [31], HCM-41 [32] and fluoro alcohols (TFE or HFIP) [33]. But some of those methods still have their own limitations in terms of yields, long reaction time, acidic or basic catalysis, tedious or difficult work-up, anhydrous organic solvents.…”