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源自1,4-恶嗪酮前体的多取代吡啶。

Polysubstituted Pyridines from 1,4-Oxazinone Precursors.

作者信息

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

机构信息

Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.

出版信息

J Org Chem. 2024 Dec 6;89(23):17635-17642. doi: 10.1021/acs.joc.4c02389. Epub 2024 Nov 12.

DOI:10.1021/acs.joc.4c02389
PMID:39532705
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11629385/
Abstract

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.

摘要

本研究描述了一种由乙炔二羧酸酯和β-氨基醇前体制备1,4-恶嗪-2-酮中间体的通用方法。以这种方式制备的恶嗪酮与模型炔烃（苯乙炔）进行串联环加成/环反转反应序列，得到取代吡啶产物。多环麦角生物碱天然产物木聚糖黑麦角碱A的合成补充了基本的反应性和选择性研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/5a3c41afa74e/jo4c02389_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/580bd77b190a/jo4c02389_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/a5b47151b927/jo4c02389_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/6787387d49a5/jo4c02389_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/240b625c0205/jo4c02389_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/5a3c41afa74e/jo4c02389_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/580bd77b190a/jo4c02389_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/a5b47151b927/jo4c02389_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/6787387d49a5/jo4c02389_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/240b625c0205/jo4c02389_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/356d/11629385/5a3c41afa74e/jo4c02389_0005.jpg

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