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Versatile Base-Catalyzed Route to Polycyclic Heteroaromatic Compounds by Intramolecular Aza-Michael Addition
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2007-06-01 , DOI: 10.1002/ejoc.200601139
Marco Bandini , Astrid Eichholzer , Magda Monari , Fabio Piccinelli , Achille Umani-Ronchi

A catalytic new synthetic approach to 3,4-dihydropyrazino[1,2-a]indol-1(2H)-ones by intramolecular 1,4-addition of readily available α,β-unsaturated esters, is described. Here, the use of a range of organic as well as inorganic bases (5–10 mol-%) allowed a fast (30 min) and regioselective ring-closing reaction to be performed in high yields under simple operational conditions. Moreover, the protocol was effectively employed, as the key step, in the synthesis of the dibromopyrrolo alkaloid derivative N-Bn-longamide b.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

中文翻译:

通过分子内氮杂-迈克尔加成制备多环杂芳族化合物的多功能碱催化途径

描述了一种通过分子内 1,4-加成容易获得的 α,β-不饱和酯来合成 3,4-二氢吡嗪并 [1,2-a]indol-1(2H)-ones 的一种新的催化合成方法。在这里,使用一系列有机和无机碱(5-10 mol%)可以在简单的操作条件下以高产率进行快速(30 分钟)和区域选择性的闭环反应。此外,该方案被有效地用作合成二溴吡咯并生物碱衍生物 N-Bn-longamide b 的关键步骤。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
更新日期:2007-06-01
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