Study on the Synthesis of Oxazolo[2,3-a]tetrahydroisoquinolines via Tandem Reaction

• Main Authors: Shih, Yu-Wei, 施郁偉
• Other Authors: Yang, Te-Fang
• Format: Others
• Language: zh-TW
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/929d5v

碩士 === 國立暨南國際大學 === 應用化學系 === 105 === 1,3-Oxazolidine frameworks were found in natural products and pharmaceutical compounds. In this research, addition of -hydroxy-,-unsaturated ketones 30 with 3,4-dihydroisoquinolines 49 provided oxazolo[2,3-a]tetrahydroisoquinoline 50 derivatives via tandem reaction involving nucleophilic addition and aza-Michael addition. The reaction proceeded under mild condition without catalyst and finished in 15 minutes, giving the various products with good to excellent yields (85-98%) and high diastereoselectivity (up to 25:1 dr). The relative stereo-structure of the products were confirmed by NMR technique and X-ray crystallography. This synthetic strategy corresponded with “green chemistry” and atomic economy.