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格氏试剂对α-酰基吡嗪鎓盐的区域选择性加成：取代的1,2-二氢吡嗪和Δ-2-氧代哌嗪的合成。

Regioselective addition of Grignard reagents to -acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ-2-oxopiperazines.

作者信息

St Hilaire Valentine R, Hopkins William E, Miller Yenteeo S, Dandepally Srinivasa R, Williams Alfred L

机构信息

Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States.

Department of Pharmaceutical Sciences, North Carolina Central University, Durham, North Carolina 27707, United States.

出版信息

Beilstein J Org Chem. 2019 Jan 8;15:72-78. doi: 10.3762/bjoc.15.8. eCollection 2019.

DOI:10.3762/bjoc.15.8
PMID:30680041
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6334805/
Abstract

The regioselective addition of Grignard reagents to mono- and disubstituted -acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45-100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ-2-oxopiperazines providing a simple and efficient approach towards their preparation.

摘要

描述了格氏试剂对单取代和二取代的α-酰基吡嗪鎓盐的区域选择性加成反应，该反应以中等至优异的产率（45 - 100%）得到取代的1,2 - 二氢吡嗪。在酸性条件下，这些1,2 - 二氢吡嗪可转化为取代的Δ-2 - 氧代哌嗪，为其制备提供了一种简单有效的方法。

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J Org Chem. 2014 Jun 20;79(12):5740-5. doi: 10.1021/jo500878v. Epub 2014 May 29.
3
Regioselective nucleophilic addition of organometallic reagents to 3-geminal bis(silyl) N-acyl pyridinium.有机金属试剂对 3-位双(硅基)N-酰基吡啶鎓的区域选择性亲核加成反应。
Org Lett. 2014 Apr 4;16(7):1880-3. doi: 10.1021/ol500302r. Epub 2014 Mar 25.
4
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J Org Chem. 2012 Apr 20;77(8):4097-102. doi: 10.1021/jo202498r. Epub 2012 Apr 2.
5
Synthesis, anticancer activity and pharmacokinetic analysis of 1-[(substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives.1-[(取代的 2-烷氧基喹喔啉-3-基)氨基甲酰基]-4-(杂)芳基哌嗪衍生物的合成、抗癌活性及药代动力学分析。
Bioorg Med Chem. 2012 Feb 1;20(3):1303-9. doi: 10.1016/j.bmc.2011.12.026. Epub 2011 Dec 27.
6
Multicomponent synthesis of fused benzimidazolopiperazines.稠合苯并咪唑并哌嗪的多组分合成。
J Org Chem. 2011 Jun 3;76(11):4728-33. doi: 10.1021/jo200397m. Epub 2011 May 10.
7
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