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

This manuscript describes an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1 H,2 H,4 H,5 H-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,...

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Published inOrganic letters Vol. 21; no. 7; pp. 1973 - 1978
Main Authors Feng, Daijun, Barton, George, Scott, Colleen N
Format Journal Article
LanguageEnglish
Published United States 05.04.2019
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Summary:This manuscript describes an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1 H,2 H,4 H,5 H-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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00019