预测新型乌吉-斯迈尔斯偶联反应：一项实验与理论相结合的研究。
Predicting new Ugi-smiles couplings: a combined experimental and theoretical study.
作者信息
Ramozzi Romain, Chéron Nicolas, El Kaïm Laurent, Grimaud Laurence, Fleurat-Lessard Paul
机构信息
Laboratoire de Chimie, UMR 5182, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie F-69364 Lyon Cedex 07 (France); Laboratoire de Chimie et Procédés, DCSO, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées ParisTech, 828, Boulevard des Maréchaux, F-91762 Palaiseau Cedex (France); Département de Chimie, UMR 8640, Ecole Normale Supérieure, 24 rue Lhomond, 75231 Paris Cedex 05 (France); Present address: Fukui Institute for Fundamental Chemistry, Kyoto University, Takano-Nishihiraki-cho 34-4, Sakyou-ku, Kyoto 606-8103 (Japan).
出版信息
Chemistry. 2014 Jul 14;20(29):9094-9. doi: 10.1002/chem.201400336. Epub 2014 Jun 5.
Following our previous mechanistic studies of multicomponent Ugi-type reactions, theoretical calculations have been performed to predict the efficiency of new substrates in Ugi-Smiles couplings. First, as predicted, 2,4,6-trichlorophenol experimentally gave the corresponding aryl-imidate. Theoretical predictions of nitrosophenols as good acidic partners were then successfully confirmed by experiments. In the latter case, the reaction offers a new access to benzimidazoles.
基于我们之前对多组分Ugi型反应的机理研究，已进行理论计算以预测新型底物在Ugi-Smiles偶联反应中的效率。首先，如预测的那样，2,4,6-三氯苯酚通过实验得到了相应的芳基亚氨酸酯。亚硝基苯酚作为良好酸性伙伴的理论预测随后通过实验得到成功证实。在后一种情况下，该反应为苯并咪唑提供了一种新的合成方法。
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