- 著者
- 野村 容朗 吉岡 義夫 南 功
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.27, no.4, pp.899-906, 1979-04-25 (Released:2008-03-31)
- 被引用文献数
- 7 13
Addition of 5-fluorouracil (1) to the double bond of 2, 3-dihydrofuran (3) without using any catalyst progressed smoothly at an elevated temperature and afforded an equilibrium mixture of 1-(tetrahydro-2-furyl)-5-fluorouracil (5) and 1, 3-bis (tetrahydro-2-furyl)-5-fluorouracil (7). By choosing favourable reaction conditions, each of these compounds was obtained in high yield. Thermal decomposition of 7 gave an equimolar mixture of 3 and 5. At a higher temperature, 5 underwent thermal reaction to yield 1 and 3. Study of the present addition reaction was extended to other 5-substituted uracils (8, R=-H, -CH3, -Cl, -Br, -COOCH3, -CONH2, -CN) which furnished the corresponding 1-(tetrahydro-2-furyl)-and 1, 3-bis (tetrahydro-2-furyl)-derivatives (9-15, 18-23) with high yields. A very small amount of 3-(tetrahydro-2-furyl)-5-substituted uracils (6, 16, 17) by-produced in the reactions was isolated and the structures unequivocally identified.