Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds,Organic Letters

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Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds
Organic Letters ( IF 4.9 ) Pub Date : 2019-03-12 00:00:00 , DOI: 10.1021/acs.orglett.9b00019
Daijun Feng ₁ , George Barton ₂ , Colleen N. Scott ₁

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This manuscript describes an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione (DMDPP), containing methyl groups at the 3,6-positions as a precursor to preparing 3,6-divinyl-substituted DPP compounds. Subsequently, following the synthesis of DMDPP, we performed an efficient and mild C–H functionalization of the methyl groups with a variety of aromatic aldehydes to synthesize the first examples of 3,6-divinyl-substituted DPP compounds in moderate to good yields.

中文翻译：

2,5-二丁基-3,6-二甲基-1 H，2 H，4 H，5 H-吡咯并[3,4- c ]吡咯-1,4-二酮：用于形成烯基二酮吡咯并吡咯的二酮吡咯并吡咯骨架化合物

该手稿描述了一种新型DPP支架2,5-二丁基-3,6-二甲基-1 H，2 H，4 H，5 H-吡咯并[3,4- c ]吡咯-1， 4-二酮（DMDPP），在3,6-位含有甲基，是制备3,6-二乙烯基取代的DPP化合物的前体。随后，在合成DMDPP之后，我们用各种芳香醛对甲基进行了有效而温和的C–H官能化，以中等至良好的产率合成了3,6-二乙烯基取代的DPP化合物的第一个实例。

更新日期：2019-03-12

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