Gazzotti Stefano, Manenti Marco, Lo Presti Leonardo, Silvani Alessandra
Dipartimento di Chimica, Universitá di Milano Via Golgi 19 Milano 20133 Italy
RSC Adv. 2019 Nov 20;9(65):37788-37800. doi: 10.1039/c9ra07712j. eCollection 2019 Nov 19.
The indium-mediated allylation of novel 3-(2-Boc-hydrazono)indolin-2-one derivatives, followed by a palladium-catalysed carboamination reaction, is described to afford unprecedented spirocyclic oxindoles in good yields. The method provides an efficient access to both and diastereoisomers of highly functionalized compounds, bearing an N-Boc, 5-substituted pyrazolidine ring at the C3-oxindole spiro junction. The versatility of the method is fully demonstrated starting from a series of substituted isatins and employing a variety of aryl halides in the key cyclization step.
本文描述了新型3-(2-叔丁氧羰基肼基)吲哚-2-酮衍生物的铟介导烯丙基化，随后进行钯催化的碳胺化反应，以良好的产率得到前所未有的螺环氧化吲哚。该方法能高效合成具有高官能化的化合物的两种非对映异构体，在C3-氧化吲哚螺环连接处带有N-叔丁氧羰基、5-取代的吡唑烷环。从一系列取代的异吲哚酮出发，并在关键的环化步骤中使用多种芳基卤化物，充分证明了该方法的通用性。
