Synthesis of chiral 2(5H)-furanone derivatives with 1,3-butadiyne structure

Autor:	Jing-Pei Huo, Jin-Feng Xiong, Zhao-Yang Wang, Pai Peng, Guang-Zhen Mo
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Solvent Ligand Chemistry Propargyl Polymer chemistry Proton NMR Organic chemistry Molecule General Chemistry Carbon-13 NMR Amino acid Catalysis
Zdroj:	Research on Chemical Intermediates. 39:4321-4335
ISSN:	1568-5675 0922-6168
Popis:	Using CuI as a catalyst, N,N-diisopropylethylamine as ligand, n-butylamine as a base, and CH3CN as solvent, the Glaser reaction of N-[5-(S)-alkoxy-2(5H)-furanonyl] amino acid propargyl esters 1 at room temperature was investigated, and a series of new chiral 2(5H)-furanone derivatives containing 1,3-butadiyne structure have been synthesized as designed, with yields of 49–84 % (mostly over 66 %). Sixteen target molecules 2 were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis. The brief synthesis of the series 2(5H)-furanones derivatives with different functional units will afford not only an important synthetic strategy for the bioactive 2(5H)-furanone derivatives as potential drug molecules but also a basis for the chiral polydiacetylene materials.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5e14373064577b9f922b7c49cd3acf6b https://doi.org/10.1007/s11164-012-0949-3 Zobrazit plný text záznamu Full text from SpringerLink