二唑雙環[2,2,2]辛烯酮之光致脫羰重排反應於合成哌嗪酸類似物之研究

Synthesis of Piperazic Acid Derivatives by Photoinduced Decarbonylative Rearrangement of Diazabicyclo[2,2,2]octenones

胡詠媜(YUNG-CHEN HU)

指導教授 ： 莊敬

中原大學/理學院/化學系/碩士(2022年)

https://doi.org/10.6840/cycu202201529

摘要

本論文係利用二唑雙環[2,2,2]辛烯酮的紫外光誘導脫羰重排反應，合成哌嗪酸衍生物。照光反應之起始物二唑雙環[2,2,2]辛烯酮76是由掩飾鄰苯醌(masked o-benzoquinones, MOBs) 7與4-苯基1,2,4-三唑雙烯酮(4-phenyl-1,2,4-triazol-3,5-dione, PTAD) 29進行分子間的Diels-Alder反應製得。接著將環加成產物溶於乙腈，並在306 nm紫外光照射下，進行Norrish Type I的脫羰重排反應可生成5,6,3-三環化合物。最後藉由聯胺移除N-苯基琥珀醯亞胺，可得到具有哌嗪酸骨架之產物。

關鍵字

??酸

並列摘要

In this study, the synthesis of piperazic acid derivatives by photoinduced decarbonylative rearrangement of diazabicyclo[2,2,2]octenones has been described. Diazabicycl[2,2,2]octenone compounds 76, the starting material of photoreaction, was prepared from the intermolecular Diels-Alder reaction of masked o-benzoquinones (MOBs) 7 with 4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) 29. Then, the cycloaddition products were transformed into 5,6,3-tricyclic compounds LXXXII in acetonitrile under UV light at 306 nm via sequential Norrish type I reaction and decarbonylative rearrangement. Removal of N-succinimide by hydrazine finally generated the piperazic acid-like products.

並列關鍵字

Piperazic Acid

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