Lutz Guilherme, Jung Juliano Ten Kathen, Back Davi Fernando, Nogueira Cristina Wayne, Zeni Gilson
Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
Laboratório de Materiais Inorgânicos, Departamento de Química, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
J Org Chem. 2022 Oct 7;87(19):12710-12720. doi: 10.1021/acs.joc.2c01255. Epub 2022 Sep 9.
This study describes the reaction of 2-amino arylalkynyl ketones with organoselenolates to form ()-vinyl selenides, which lead to 4-organoselenyl quinolines via an intramolecular condensation. Using the optimized reaction conditions, the generality of this cyclization was studied with various arylalkynyl ketones and diorganyl diselenides. The study of the reaction mechanisms led to the isolation and identification of a vinyl selenide, which was the key intermediate for this cyclization. To expand the structural diversity and to demonstrate the applicability of the 4-organoselenyl quinolines prepared, we studied their application as substrates in the cleavage of the carbon-selenium bond using -butyllithium followed by the capture of the lithium intermediate by electrophiles and Suzuki and Sonogashira cross-coupling reactions.
本研究描述了2-氨基芳基炔基酮与有机硒醇盐反应生成（）-乙烯基硒醚，后者通过分子内缩合生成4-有机硒基喹啉。使用优化的反应条件，用各种芳基炔基酮和二有机基二硒醚研究了这种环化反应的通用性。对反应机理的研究导致分离和鉴定了一种乙烯基硒醚，它是这种环化反应的关键中间体。为了扩大结构多样性并证明所制备的4-有机硒基喹啉的适用性，我们研究了它们作为底物在使用丁基锂裂解碳-硒键，随后通过亲电试剂捕获锂中间体以及铃木和薗头交叉偶联反应中的应用。
