期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 7, 期 22, 页码 18630-18639出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.9b05073
关键词
anise oil; aza Diels-Alder reaction; deep eutectic solvents; diastereoselective synthesis; tetrahydroquinolines
资金
- Universidad industrial de Santander
- Universidad Nacional de Colombia
In this contribution, a sustainable one-pot diastereoselective synthesis of tetrahydroquinolines through the aza Diels-Alder reaction is reported starting from star anise oil, substituted anilines, and aromatic aldehydes in a choline chloride/zinc chloride eutectic mixture as new reaction media. Star anise extracts and essential oils obtained by Soxhlet, ultrasound-assisted extraction, steam distillation, and hydrodistillation were analyzed by gas chromatography-mass spectrometry finding the highest content of trans-anethol from hydrodistillation; in addition, the eutectic composition and temperature for the choline chloride/zinc chloride mixture were revisited. All the compounds were obtained in 28-98% yield with diastereoselectivity toward the cis-(2e,4e) product. Furthermore, the deep eutectic solvent was reused in three cycles without observing a detrimental catalytic activity, and green metric analysis showed a favorable environmental impact of this synthetic method.
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