? ?嵌入氯化五并苯?酯之芳香性親核胺基化反應

Amination of Quinoxaline-Embedded Chlorinated Pentacenoquinone Ester via Nucleophilic Aromatic Substitution

陳濬昌(Jyun-chang Chen)

指導教授 ： 周德璋

朝陽科技大學/理工學院/應用化學系碩士在職專班/碩士(2012年)

摘要

利用六氯環戊二烯(44)為起始物製備5,5-二甲氧基-1,2,3,4-四氯環戊二烯(13)。之後與1,4-苯?(14a)進行狄爾斯–亞德環加成反應，可得到環加成物15a，再利用釕催化之氧化反應生成鄰-二酮水合物46，將鄰-二酮水合物與鄰-苯二胺進行縮合反應，再進行酸性或鹼性條件下之一鍋化的促化裂解反應，得到?

關鍵字

? ? ； 五并苯?酯 ； 芳香性親核反應

並列摘要

Hexachlorocyclopentadiene (44) was used as a starting material to synthesize 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene (13). The Diels–Alder cycloaddition of 1,4-benzoquinone (14a) and 13 produces adduct 15, which was then converted to by ruthenium-promoted oxidation reaction to o-dione hydrate 46. The condensation reaction of 46 with an arene-1,2-diamine produces 48. The fragmentation of compound 48 was carried out in one-pot in acidic or basic conditions to produce quinoxaline-embedded chlorinated pentacenoquinone ester 35. The reactions of 35 with 61a and 61b via nucleophilic aromatic substitution produce target products 62a and 62b.
The photophysical properties of 62a and 62b were examined in chloroform. The fluorescence of each compound was identical with the references. The results revealed that 62a and 62b lack intramolecular interaction, but have intramolecular pi-pi interaction from examination of the X-Ray crystal structures.

並列關鍵字

quinoxaline ； nucleophilic aromatic substitution ； pentacenoquinone ester

參考文獻

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