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作为用于合成γ-杂环的碳合成子的N,N-二甲基甲酰胺:吡咯并/吲哚并[1,2 - a]喹喔啉和喹唑啉-4-酮

,-Dimethylformamide as Carbon Synthons for the Synthesis of -Heterocycles: Pyrrolo/Indolo[1,2-]quinoxalines and Quinazolin-4-ones.

作者信息

Li Shichen, Ren Jianing, Ding Chengcheng, Wang Yishou, Ma Chen

机构信息

School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. China.

出版信息

J Org Chem. 2021 Dec 3;86(23):16848-16857. doi: 10.1021/acs.joc.1c02067. Epub 2021 Nov 22.

Abstract

,-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered that -methyl and -acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

摘要

作为合成前体,特别是贡献甲基、酰基和氨基的N,N-二甲基甲酰胺(DMF)在杂环合成和官能团化中发挥了重要作用。在本方法中,通过使用单质碘,在无任何金属或过氧化物的情况下,以中等至良好的产率获得了多种吡咯并/吲哚并[1,2 -]喹喔啉和喹唑啉-4-酮。我们认为DMF的N-甲基和N-酰基通过不同机制分别参与并完成反应,这显示出DMF仍有待探索的潜力。

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