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曼尼希碱作为烯酮前体用于水介导高效合成2,3,6-三取代吡啶和5,6,7,8-四氢喹啉。

Mannich Bases as Enone Precursors for Water-Mediated Efficient Synthesis of 2,3,6-Trisubstituted Pyridines and 5,6,7,8-Tetrahydroquinolines.

作者信息

Hanashalshahaby Essam Hamied Ahmed, Unaleroglu Canan

机构信息

Hacettepe University, Chemistry Department, 06800 Beytepe, Ankara Turkey.

出版信息

ACS Comb Sci. 2015 Jun 8;17(6):374-80. doi: 10.1021/acscombsci.5b00046. Epub 2015 May 26.

Abstract

A highly efficient, regioselective, and environmentally friendly method has been developed for water-mediated synthesis of 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines. The introduced method allows easy preparation of various polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines via domino reaction of an enolizable ketone, ammonia and enones derived from different Mannich bases in mild reaction conditions. Montmorillonite K-10 promoted this one-pot three-component reaction and gave both new and known 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines in good yields. The reaction protocol provides a wide array of functionality in construction of polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines from commercially available starting materials in easily applicable and environmentally friendly conditions.

摘要

已开发出一种高效、区域选择性且环境友好的方法,用于水介导的2,3,6-三取代吡啶和5,6,7,8-四氢喹啉的合成。所引入的方法能够在温和的反应条件下,通过可烯醇化酮、氨与源自不同曼尼希碱的烯酮的多米诺反应,轻松制备各种多取代吡啶和5,6,7,8-四氢喹啉。蒙脱石K-10促进了该一锅三组分反应,并以良好的产率得到了新的和已知的2,3,6-三取代吡啶以及5,6,7,8-四氢喹啉。该反应方案在易于应用且环境友好的条件下,从市售起始原料构建多取代吡啶和5,6,7,8-四氢喹啉时提供了广泛的官能团。

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