Base-mediated intramolecular cyclization of (2-propargyl ether) arylimines: an approach to 3-amino-benzofurans |
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Authors: | Rafaela Gai,Thaí s Prochnow,Davi F. Back,Gilson Zeni |
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Affiliation: | 1. Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil;2. Laboratório de Materiais Inorgânicos, CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil |
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Abstract: | We present here a practical synthesis of functional 3-amino-benzofurans through base-promoted intramolecular cyclization of (2-propargyl ether) arylimines. A systematic study of the cyclization system revealed that the presence and the amount of base played an essential role in this reaction. The results showed that the cyclization proceeded cleanly and smoothly under mild reaction conditions, employing potassium tert-butoxide as base, THF as solvent, at room temperature in a short reaction time (1 h). The generality of this reaction has been established with (2-propargyl ether) arylimines having both electron-withdrawing and electron-donating groups. |
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Keywords: | Cyclization Benzofurans Heterocycles |
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