Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
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DOI：
10.1021/jo4007199
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发表时间：
2013-06-21
影响因子：
3.6
通讯作者：
Mancheno, Olga Garcia
中科院分区：
文献类型：
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作者：
Rohlmann, Renate;Stopka, Tobias;Mancheno, Olga Garcia
以克里思氧代铵盐为温和无毒的氧化剂，以N-烷基苯胺为起始原料，采用铁催化的趋异氧化串联法合成了二氢喹唑啉和喹啉。Fe（OTf）（2）是用于形成二氢喹唑啉的选择的刘易斯酸催化剂，而FeCl 3导致喹啉合成的更好结果。这种不同的方法意味着，对于两种合成，N-烷基苯胺的α-C（sp（3））-H键的直接氧化官能化发生，分别在均缩合或与简单烯烃反应时导致C-N键形成或C-C键形成。环化后，最后的氧化生成这些有趣的生物活性杂环类在一个合成转化。此外，在这些温和的氧化条件下，还成功地开发了由苯胺、醛和烯烃一锅多组分合成喹啉的方法。
A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf)(2) was the Lewis acid catalyst of choice for the formation of dihydroquinazoline, whereas FeCl3 led to better results for the synthesis of quinolines. This divergent approach implies that, for both syntheses, direct oxidative functionalization of a alpha-C(sp(3))-H bond of the N-alkylanilines occurs, leading to C-N bond formation or C-C bond formation upon homocondensation or reaction with simple olefins, respectively. Cyclization followed by a final oxidation generates these classes of interesting bioactive heterocycles in one synthetic transformation. Additionally, the one-pot multicomponent synthesis of quinolines from anilines, aldehydes, and olefins has also been successfully developed under these mild oxidative conditions.