N,3-二芳基丙炔酰胺在超亲电活化作用下与芳烃的反应：4,4-二芳基-3,4-二氢喹啉-2(1H)-酮及其衍生物的合成
Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives.
作者信息
Gurskaya Larisa Yu, Belyanskaya Diana S, Ryabukhin Dmitry S, Nilov Denis I, Boyarskaya Irina A, Vasilyev Aleksander V
机构信息
Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Science, ul. Lavrentieva 9, Novosibirsk, 630090, Russia.
Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
出版信息
Beilstein J Org Chem. 2016 May 11;12:950-6. doi: 10.3762/bjoc.12.93. eCollection 2016.
The reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44-98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the superelectrophilic activation of the N-formyl group by TfOH in the reaction with benzene resulted in the formation of N-(diphenylmethyl)-substituted dihydroquinolinones.
3-芳基-N-(芳基)丙炔酰胺与芳烃在三氟甲磺酸（TfOH）存在下于室温反应0.5小时，生成4,4-二芳基-3,4-二氢喹啉-2-(1H)-酮，产率为44-98%。所得到的二氢喹啉酮进一步转化为相应的N-酰基或N-甲酰基衍生物。对于后者，在与苯的反应中，三氟甲磺酸对N-甲酰基的超亲电活化导致形成N-(二苯甲基)取代的二氢喹啉酮。
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