10.3762/BJOC.16.144
The research presents a convergent strategy for synthesizing nitrogen-containing heterocycles, specifically indole, indolone, and cinnoline derivatives, from common 1,4-diketone and primary amine substrates. The authors demonstrate that by varying the substrates, substituents, or heating mode, they can selectively produce these derivatives in moderate to excellent yields. The study involves the preparation of variously substituted 1,4-diketones through Nef and Wittig reactions. The synthesis of indole and indolone derivatives is explored under different conditions, with the reaction mechanism involving imine formation and subsequent 1,2- or 1,4-addition processes. The synthesis of cinnoline derivatives is optimized using hydrazine monohydrate and acetic acid in ethanol under reflux conditions. The developed protocols are mild, metal-free, and functional-group tolerant, making them suitable for medicinal chemistry applications.
10.3987/COM-90-5442
The study detail the first synthesis of thienotriazolothiazepines, a novel heteroazepine derivative with anti-PAF (platelet activating factor) activity. The researchers synthesized these compounds to explore their potential as potent and orally active PAF antagonists. The synthetic route involved several steps, including the formation of 2-aminothiophenes, protection and reduction of amino groups, Mitsunobu conditions to form sulfides, hydrolysis to carboxylic acids, cyclization to form thiazepine rings, and the construction of triazole rings using Lawesson's reagent and subsequent treatments with hydrazine monohydrate and trimethyl orthoacetate. The synthesized thienotriazolothiazepines were tested for their ability to inhibit rabbit platelet aggregation induced by PAF, and all compounds exhibited anti-PAF activity. The study concludes that the synthesized compounds are effective in inhibiting PAF-induced platelet aggregation, suggesting their potential as therapeutic agents for conditions related to platelet aggregation.