Laboratory of Bioorganic Chemistry & Membrane Biophysics (L.O.B.O.), School of Veterinary Sciences , University of Extremadura , Cáceres 10003 , Spain.
J Org Chem. 2019 Jun 7;84(11):7426-7433. doi: 10.1021/acs.joc.9b00381. Epub 2019 May 14.
We report an easy multicomponent synthesis of polycyclic isoindoles from cyclic 1,3-dicarbonyls, aldehydes, isocyanides, and maleimides. The key step consists of the one-pot Diels-Alder trapping of a reactive 2-aminofuran intermediate, formed by a sequence of a Knoevenagel condensation and a [4+1] cycloaddition. Moreover, a further microwave-promoted dehydrogenative N-C bond forming reaction allows the straightforward synthesis of a natural product like isoindolocarbazole, validating the utility of our methodology to obtain isoindoles as useful intermediates for the synthesis of complex polycyclic molecules.
我们报道了一种从环状 1,3-二羰基化合物、醛、异氰化物和马来酰亚胺出发的多环异吲哚的简便多组分合成方法。关键步骤包括一锅法 Diels-Alder 捕获反应，其中涉及到一个活性 2-氨基呋喃中间体的形成，该中间体是通过 Knoevenagel 缩合和 [4+1] 环加成反应序列形成的。此外，进一步的微波促进脱氢 N-C 键形成反应允许直接合成天然产物类似异吲哚咔唑，验证了我们的方法在获得异吲哚作为复杂多环分子合成有用中间体方面的实用性。
