Several investigations were carried on the modification of tacrine (THA), an acetyl cholinesterase inhibitor, used in the treatment of Alzheimer's disease. THA can be prepared by several methods, among those Friedlander condensation is the simplest and convenient approach. As an attempt to synthesize tacrine analogues with less/no hepatotoxicity, we designed some novel thienopyridine derivatives by incorporating terpenoids into the structure. From the designed series, we synthesized three tetracyclic THA analogues by conventional and microwave methods using different catalysts in the presence/absence of solvent. We found the formation of byproducts and some charged species along with desired THA analogues. The reaction mixture was subjected to LC-MS and the title compounds were confirmed. Promising yields were found with anhydrous aluminum chloride in dichloroethane.
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