茚衍生物以氧氣為氧化劑合成異喹啉之研究

Synthesis of Isoquinoline via Aerobic Oxidation of Indene Derivatives

陳致壬(Chih-Jen Chen)

指導教授 ： 莊敬

中原大學/理學院/化學研究所/碩士(2014年)

https://doi.org/10.6840/cycu201400759

摘要

本研究以茚衍生物作為起始物，以尿素為氮來源，於氧氣下進行一鍋化反應，合成一系列相對應之異喹啉。研究中發現，以1,4-二噁烷與甲苯混和比例為3：2作為溶劑時反應性最佳，而加入過渡金屬不會幫助此反應進行。一般合成異喹啉衍生物需在強酸條件或以過渡金屬作為催化劑進行反應，而本實驗中無需金屬催化劑，且反應條件也較為溫和。

關鍵字

氧氣 ； 異喹啉 ； 茚

並列摘要

The purpose of this study was to investigate the synthesis of isoquinolines, from indene derivatives with urea and oxygen via one-pot reaction. It was found that the best yield was obtained by using of a 3:2 mixture of 1,4-dioxane and toluene as solvent. Transition metal catalyst was not needed in this reaction. Previausly reported syntheses of isoquinoline derivatives were carried out in acidic conditions or needed a transition metal as catalyst in the reaction. In this research, out method is metal-free and the reaction condition is relativily mild.

並列關鍵字

Aerobic Oxidation ； Indene ； Isoquinoline

參考文獻

1. Liu, J. K.; Couldwell, W. T. Neurocritical care 2005, 2, 124.

5. (a) Pictet, A.; Spengler, T. Eur. J. Inorg. Chem. 1911, 44, 2030; (b) Stockigt, J.; Antonchick, A. P.; Wu, F.; Waldmann, H. Angew. Chem. Int. Ed. Engl. 2011, 50, 8538.

6. Brown, E. V. J. Org. Chem. 1977, 42, 3208.

7. Gill, E. W.; Bracher, A. W. J. Heterocycl. Chem. 1983, 20, 1107.

10. Fremery, M. I.; Fields, E. K. J. Org. Chem 1964, 29, 2240.