Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

文献信息

发布日期 2023-12-05

DOI 10.1039/D3OB01620J

影响因子 3.876

作者

Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst

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摘要

Two tandem catalytic systems are described for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts as starting materials. 4-Aryl-3-pyrrolyl- and 4-aryl-3-indolyl-maleimides were successfully obtained via a Pd(OAc)2/PPh3 based protocol. In contrast, maleimide-fused pyrrolo and indolo[1,2-a]quinolines were obtained in a complementary methodology using CuI/L-proline. These strategies involved a combination of benzylic amine oxidation, trans-amidation, intramolecular Knoevenagel condensation, and N-arylation reactions. Computational investigations provide further insights into this reaction sequence.

期刊推荐

Current Pharmaceutical Biotechnology

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Foundations of Chemistry

Angewandte Chemie International Edition

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来源期刊

Organic & Biomolecular Chemistry

CiteScore: 3.4

自引率: 10.3%

年发文量: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

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Contents list

Synthesis of amino alcohols, cyclic urea, urethanes, and cyclic carbonates and tandem one-pot conversion of an epoxide to urethanes using a Zn–Zr bimetallic oxide catalyst

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来源期刊

Organic & Biomolecular Chemistry

推荐化合物

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