Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South Africa.
Org Biomol Chem. 2019 Feb 20;17(8):2204-2211. doi: 10.1039/c8ob03040e.
A simple and efficient method for the one-pot synthesis of novel 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes via the Vilsmeier-Haack reaction of the corresponding 7-acetyl-2-arylindoles has been developed. The mechanism of this reaction is envisaged to involve initial C-3 formylation and subsequent diformylation at the acetyl group with the excess Vilsmeier-Haack reagent followed by heteroannulation of the six-membered ring with concomitant extrusion of dimethylamine to afford the 1,2,5,8-tetrasubstituted pyrroloquinolinones. The highlight of this method is the construction of carbon-carbon and carbon-nitrogen bonds in a single-pot operation to afford polycarbo-substituted pyrroloquinolinones.
通过相应的 7-乙酰基-2-芳基吲哚的 Vilsmeier-Haack 反应，开发了一种用于一锅法合成新型 6-氧代-6H-吡咯并[3,2,1-ij]喹啉-1,5-二醛的简单高效的方法。该反应的机理设想包括初始的 C-3 甲酰化，随后用过量的 Vilsmeier-Haack 试剂在乙酰基处进行二甲酰化，然后六元环杂环化，同时释放二甲胺，得到 1,2,5,8-四取代的吡咯并喹啉酮。该方法的亮点在于在一锅操作中构建碳-碳和碳-氮键，以得到多碳取代的吡咯并喹啉酮。
