A highly efficient and regioselective synthesis of furo[3,4‐c]isoquinoline‐1,5(3H,4H)‐diones and furo[3,4‐b]pyridine‐2,5(1H,7H)‐diones via Rh(III)‐catalyzed one‐pot cascade reactions of aromatic/vinylic N‐alkoxyamides with 4‐hydroxy‐2‐alkynoates is presented. Mechanistically, the formation of the title compounds is triggered by a Rh(III)‐catalyzed inert C(sp²)−H bond activation of the amide substrate followed by its [4+2] annulation and lactonization with 4‐hydroxy‐2‐alkynoate featuring with an oxidizing and partially traceless directing group. To the best of our knowledge, this is the first example in which both the furan‐2(5H)‐one and the pyridin‐2(1H)‐one scaffolds are constructed in one pot under one set of reaction conditions. Compared with literature methods, notable features of this new protocol include facile formation of bis‐heterocyclic scaffolds from readily available acyclic substrates, broad substrate scope with good tolerance of a wide range of functional groups, excellent regioselectivity and high efficiency.

中文翻译：

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通过Rh / III催化的芳族/文酸N-烷氧基酰胺与4-羟基-2-炔烃的级联反应一锅合成N，O-杂环

呋喃并[3,4- c ]异喹啉-1,5 （3 H，4 H）-二酮和呋喃并[3,4- b ]吡啶-2,5（1 H，7 H）的高效区域选择性合成介绍了通过Rh（III）催化的芳族/乙烯基N-烷氧基酰胺与4-羟基-2-炔基酯的一锅级联反应的二酮。从机理上讲，Rh（III）催化的惰性C（sp ²）-H键活化酰胺底物，然后使其[4 + 2]环化并用具有氧化和部分无痕导向基团的4-羟基-2-炔基内酯进行内酯化。就我们所知，这是第一个实例，其中在一组反应条件下，在一个锅中构建了呋喃2（5 H）-1和吡啶2（1 H）-1支架。与文献方法相比，该新方案的显着特征包括从易于获得的无环底物轻松形成双杂环支架，宽广的底物范围和对各种官能团的良好耐受性，极佳的区域选择性和高效率。