Cu-Catalyzed Decarboxylative Annulation of N-Phenylglycines with Maleimides: Synthesis of 1H-Pyrrolo[3,4-c]quinoline-1,3(2H)-diones,The Journal of Organic Chemistry

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Cu-Catalyzed Decarboxylative Annulation of N-Phenylglycines with Maleimides: Synthesis of 1H-Pyrrolo[3,4-c]quinoline-1,3(2H)-diones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-02-08 , DOI: 10.1021/acs.joc.2c02757
Kai-Hong Lv ₁ , Li Chen ₁ , Ke-Hua Zhao ₁ , Jia-Ming Yang ₁ , Sheng-Jiao Yan ₁

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A novel protocol for the construction of functionalized 1H-pyrrolo[3,4-c]quinoline-1,3(2H)-diones (PQLs, 3) from N-phenylglycines and maleimides was developed. The cascade reaction was enabled by heating a mixture of the two substrates in the presence of di-tert-butyl peroxide (DTBP) as an oxidant and anhydrous CuBr as a catalyst in chlorobenzene. Consequently, a diverse series of PQLs 3 were synthesized in moderate-to-good yields (43–73%). The synthesis of the PQLs was enabled via a one-pot cascade reaction that proceeded through subsequent oxidative decarboxylation, 1,2-addition, intramolecular cyclization, tautomerization, and aromatization reactions. This protocol can be used for the synthesis of functionalized PQLs via a one-pot oxidative decarboxylation annulation reaction rather than through a series of multistep reactions, making it suitable for both combinatorial and parallel syntheses of PQLs.

中文翻译：

Cu 催化的 N-苯基甘氨酸与马来酰亚胺的脱羧环化：1H-吡咯并[3,4-c]喹啉-1,3(2H)-二酮的合成

开发了一种用于从N -苯基甘氨酸和马来酰亚胺构建功能化 1 H -吡咯并[3,4- c ]喹啉-1,3(2 H )-二酮 (PQLs, 3 )的新方案。在二叔丁基过氧化物 (DTBP) 作为氧化剂和无水 CuBr 作为催化剂存在的情况下，在氯苯中加热两种底物的混合物，从而实现级联反应。因此，一系列不同的 PQL 3以中等到良好的收率 (43–73%) 合成。PQL 的合成是通过一锅级联反应实现的，该反应通过随后的氧化脱羧、1,2-加成、分子内环化、互变异构和芳构化反应进行。该协议可用于通过单锅氧化脱羧环化反应而不是通过一系列多步反应来合成功能化 PQL，使其适用于 PQL 的组合和平行合成。

更新日期：2023-02-08

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