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Updated: Aug 29, 2025
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Stereoselective Reduction of Alkynes: Synthesis of 4-Organoselenyl Quinolines
Guilherme Lutz1, Juliano Ten Kathen Jung1, Davi Fernando Back2
1Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
Abstract:
This study describes the reaction of 2-amino arylalkynyl ketones with organoselenolates to form (Z)-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 n-butyllithium followed by the capture of the lithium intermediate by electrophiles and Suzuki and Sonogashira cross-coupling reactions.
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