設計與合成1,2-二氫-3-氧喹唑啉衍生物及其光化學反應研究

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Title:	設計與合成1,2-二氫-3-氧喹唑啉衍生物及其光化學反應研究
Other Titles:	Design and synthesis of 1,2-dihydroquinazoline 3-oxide derivatives and their photochemical properties
Authors:	陳奕州 Yi-Chou, Chen
Contributors:	楊定亞 Ding-Yah, Yang 化學系
Keywords:	?唑?衍生物 1,2-dihydroquinazoline 3-oxide derivatives
Date:	2013
Issue Date:	2015-03-06T07:33:18Z (UTC)
Abstract:	1-(2-胺基苯基)苯乙酮?與苯甲醛衍生物經由縮合-合環反應，合成出一系列的1,2-二氫?唑?衍生物，並研究其光敏感特性。在氰甲烷中以可見光照射化合物進行脫水反應，得到?唑?衍生物，探討其照光反應合理的反應機構。其中2-(對硝基苯)取代的化合物不具光敏感特性，在照光中加入金屬釕光氧化還原催化劑會使化合物進行氧化作用，利用三氯化磷可以達到脫氧的效果，進一步得到?唑?衍生物。其次，我們合成出一系列的1,2-二氫?唑?衍生物，其中一號氮位置上有甲基取代的化合物也具備光敏感特性，以可見光或紫外線照射後會產生顏色上的變化，唯此光化學反應不具可逆性且照光後之產物結構仍有待確認。最後，我們於此1,2-二氫?唑?分子設計一個七圓環的分子內氫鍵，成功的使其光致變色性質具可逆性。 A series of 1,2-dihydroquinazoline 3-oxides were synthesized via the condensation of 1-(2-aminophenyl)ethanone oxime with various aryl aldehydes to investigate their visible light-sensitive properties. Upon visible light irradiation in acetonitrile, 1,2-dihydroquinazoline 3-oxides underwent dehydration to give the corresponding quinazolines. The only exception was the 2-(p-nitrophenyl)-substituted substrate, which is insensitive to visible light. This compound could be first oxidized to quinazoline 3-oxide via ruthenium-catalyzed visible light photoredox catalysis, and followed by treating with PCl3 to yield the corresponding quinazoline. Next, several N-methyl 1,2-dihydroquinazoline 3-oxides were also synthesized to evaluate their light-sensitive properties. Our studies indicated that the prepared compounds are indeed light-sensitive and change from colorless to red upon UV irradiation. Nevertheless, the photoreaction is irreversible, and the structure of the photogenerated product remains to be confirmed. Finally, we introduced a seven-membered ring intramolecular hydrogen bonding onto the 1,2-dihydroquinazoline 3-oxide. The preliminary study suggested that the resulting compound exhibits the desired photochromic properties, that is, the photogenerated product can be reverted back to the starting material when sat in the dark for some time.
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