Refernces
10.1021/jo9025644
The research focuses on the development of a copper-catalyzed annulation reaction between 2-formylazoles and o-aminoiodoarenes, leading to the synthesis of substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. This method provides a one-step route to these biologically active molecules, which are present in a growing number of pharmaceutical compounds. The reaction conditions were optimized using 2-iodoaniline and 2-formylpyrrole as starting materials, with the best results obtained using 1 equivalent of 2-formylpyrrole, 1.5 equivalents of 2-iodoaniline, 2 equivalents of K3PO4, 10 mol % CuI, 20 mol % sparteine, and NMP as the solvent at 130°C for 24 hours. The reaction was found to be effective for a variety of substituted aminoiodoarenes and formylazoles, including 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole. The synthesized products were analyzed using techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS) to confirm their structures and purities.
10.1016/j.tet.2008.07.029
This research presents a novel four-step synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system. The purpose of this study is to develop an efficient and straightforward route to synthesize this ring system, which is structurally related to the pharmacologically important 1,4-benzodiazepine central nervous system agents. The synthesis involves alkylation of 1H-pyrrole-2-carbaldehyde with ethyl or methyl bromoacetate, oxidation of the resulting esters with potassium permanganate, conversion of the acids to acid chlorides using thionyl chloride, and finally a Dieckmann condensation to form the pyrrolo[2,1-c][1,4]benzodiazocine ring. The study concludes that this new synthetic route is efficient and provides a practical method for the synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system, potentially facilitating further research and development of related pharmaceutical compounds.
10.1021/jo048204b
The study presents a novel synthetic method for the creation of heterocyclic structures containing a pyrrolo[1,2-a][1,4]diazepine fragment, utilizing a modified four-component Ugi condensation reaction. The chemicals used in the study include aldehydes, amines, isonitriles, and carboxylic acids, which serve as the four components for the Ugi reaction. Additionally, bifunctional reagents such as aminocarboxylates and 1H-pyrrol-1-yl derivatives were synthesized and converted into 2-formyl-1H-pyrroles and aldehyde acids, which are key intermediates in the process. The purpose of these chemicals is to demonstrate the versatility and usefulness of the developed synthetic approach for creating variously substituted compounds, which have potential pharmaceutical properties, particularly as antitumor agents and central nervous system (CNS) active agents. The study also discusses the scope and limitations of the chemistry involved and provides a valuable source of novel physiologically active agents.
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