Synthesis of Tetrahydroisoquinolines via Intramolecular Diels-Alder Reaction of Furans with Allenylamines

• Main Authors: Du, Wen-Pine, 杜文平
• Other Authors: Wu, Hsien-Jen
• Format: Others
• Language: zh-TW
• Published: 2002
• Online Access: http://ndltd.ncl.edu.tw/handle/97352479916973130849

碩士 === 國立交通大學 === 應用化學系 === 90 === Synthesis of Tetrahydroisoquinolines via Intramolecular Diels-Alder Reaction of Furans with Allenylamine Student : Du, Wen-Pine Advisor : Dr. Wu, Hsien-Jen Institute of Applied Chemistry National Chiao Tung University Abstract The skeleton of tetrahydroisoquinoline 11, 13, 16 via intramolecular Diels-Alder reaction of furan diene with propargyl amine was synthesized, successfully. And we also study the influence of hetroatom to intramolecular Diels- Alder reaction. In the series of nitrogen, when the substituent is hydrogen or methyl group, we can isolate the cycloadduct 6 and 23, directly. In the series of nitrogen and oxygen, when the substituent is methylthio group we all isolate ring opening product 35, 42, 54, directly, and we don’t obtain the cycloadduct. In here, we propose a proper machanism of intramolecular Diels-Alder reaction product, and use methylsulfonyl and methylsulfinyl group, 62 and 67 to prove the machanism. But we don’t obtain the positive evidence. We only obtain the elimination product.