10.1016/j.tet.2007.11.036
The study presents a two-step synthesis method for benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives, utilizing a domino Knoevenagel condensation/intramolecular hetero-Diels-Alder reaction sequence. The process involves an initial intermolecular Knoevenagel condensation of a compound with active methylene compounds to form a heterodiene, which then undergoes intramolecular hetero-Diels-Alder cycloaddition. The research successfully optimized the reaction conditions, including the choice of catalyst and solvent, to achieve high yields of the desired products. The method demonstrates a novel route for constructing complex heterocycles with potential applications in medicinal chemistry.
10.1021/jo01310a057
The research explores the synthesis and reactions of various organic compounds. It includes the preparation of indole derivatives using compounds like 1-methyl-2-vinylpyrrole, methyl propiolate, and hydroquinone, resulting in products such as dimethyl indole-6,7-dicarboxylate and methyl 1-tert-butylindole-7-carboxylate, characterized by melting points, IR spectra, NMR spectra, and elemental analysis. Additionally, the study introduces alkyl and aryl α-methoxyvinyl carbonates (3a-c) as efficient reagents for carboalkoxylation and carboaryloxylation of amines, including weakly basic ones, under mild conditions, yielding high-quality N-carboalkoxylated and N-carboaryloxylated compounds. The research also examines the reactions of [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]dimethylammonium chloride with hydrazines and amidines, producing 1,2,4-triazoles and substituted products, with detailed spectral data confirming the structures of the synthesized compounds.
10.1055/s-0028-1088004
The research presents a novel three-component coupling (3CC) reaction involving isoquinoline, activated alkynes, and nitromethane, which produces nitromethyl derivatives of 1,2-dihydroisoquinolines in high yields and with high selectivity. This reaction is notable for its simplicity and mild conditions, as it proceeds smoothly at 25 °C without the need for a catalyst. The study explores the coupling of various substituted isoquinolines and quinolines with different activated alkynes, such as methyl propiolate, ethyl propiolate, and dimethyl acetylenedicarboxylate, yielding the desired products in good to excellent yields. The reaction mechanism is proposed to involve a zwitterionic intermediate. The products are characterized using NMR, IR, and mass spectrometry, confirming the successful synthesis of these nitromethyl derivatives. This method offers significant advantages, including operational simplicity, high product yields, and tolerance of various functional groups, making it a valuable tool for the synthesis of 1-substituted dihydroisoquinolines and 2-substituted quinolines.
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