1,4-恶嗪酮前体的多取代吡啶

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-11-12 DOI:10.1021/acs.joc.4c0238910.1021/acs.joc.4c02389

L. C. Thompson, Adrianne M. Kinsey, Zannatul Shahla and Jonathan R. Scheerer*,

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引用次数: 0

摘要

本文介绍了由二羧酸乙炔和β-氨基醇前体制备1,4-恶嗪-2-酮中间体的一般方法。以这种方法制备的恶嗪酮与模型炔（苯基乙炔）进行串联环加成/环还原反应，得到取代吡啶产物。基本的反应性和选择性研究补充了多环麦角生物碱天然产物木聚糖内酯A的合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Polysubstituted Pyridines from 1,4-Oxazinone Precursors

This study describes a general method for the preparation of 1,4-oxazin-2-one intermediates from acetylene dicarboxylate and β-amino alcohol precursors. Oxazinones prepared in this manner were employed in a tandem cycloaddition/cycloreversion reaction sequence with a model alkyne (phenyl acetylene) to give substituted pyridine products. Fundamental reactivity and selectivity studies are complemented by the synthesis of the polycyclic ergot alkaloid natural product xylanigripone A.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.