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Issue 36, 2018
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Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3 + 2] annulation of azomethine ylides with allenoates

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Abstract

A convenient [3 + 2] annulation of azomethine ylides with allenoates promoted by triethylamine produced highly functionalized 2,5-dihydropyrrole derivatives in moderate to excellent yields under mild conditions. The potential utility of this reaction indicates that this reaction could be performed on the gram scale and the synthesized functionalized 2,5-dihydropyrrole derivatives could be further transformed into other interesting heterocycles. The mechanism for the transformation is a tandem β-addition/Mannich cyclization process.

Graphical abstract: Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3 + 2] annulation of azomethine ylides with allenoates

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Publication details

The article was received on 09 Aug 2018, accepted on 28 Aug 2018 and first published on 28 Aug 2018


Article type: Communication
DOI: 10.1039/C8OB01946K
Citation: Org. Biomol. Chem., 2018,16, 6638-6646

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    Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3 + 2] annulation of azomethine ylides with allenoates

    Z. Huang, Z. Dai, J. Zhu, F. Yang and Q. Zhou, Org. Biomol. Chem., 2018, 16, 6638
    DOI: 10.1039/C8OB01946K

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