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硝基亚乙烯基 Morita-Baylis-Hillman 乙酸酯与咪唑并吡啶的合成及阿普唑仑和唑吡坦的便捷合成。

Synthesis of imidazopyridines from the Morita-Baylis-Hillman acetates of nitroalkenes and convenient access to Alpidem and Zolpidem.

机构信息

Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.

出版信息

Org Lett. 2012 Sep 7;14(17):4580-3. doi: 10.1021/ol3020418. Epub 2012 Aug 24.

Abstract

A variety of functionalized imidazo[1,2-a]pyridines have been synthesized through a one-pot, room temperature, and reagent-free reaction between MBH acetates of nitroalkenes and 2-aminopyridines. The reaction involves a cascade inter-intramolecular double aza-Michael addition of 2-aminopyridines to MBH acetates. Our methodology is marked by excellent yield, regioselectivity and, above all, adaptability to synthesize imidazopyridine-based drug molecules such as Alpidem and Zolpidem.

摘要

通过硝基亚乙烯基 MBH 乙酸盐与 2-氨基吡啶之间的一锅、室温、无试剂反应,合成了各种功能化的咪唑并[1,2-a]吡啶。该反应涉及 2-氨基吡啶到 MBH 乙酸盐的级联内-分子内双氮杂迈克尔加成。我们的方法具有产率高、区域选择性好、最重要的是适应性强等优点,可用于合成基于咪唑并吡啶的药物分子,如阿普唑仑和唑吡坦。

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