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铜介导的N-烯基-α,β-不饱和硝酮的合成及其向三取代和四取代吡啶的转化。

Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

作者信息

Kontokosta Dimitra, Mueller Daniel S, Mo Dong-Liang, Pace Wiktoria H, Simpson Rachel A, Anderson Laura L

机构信息

Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL 60607, U.S.A.

出版信息

Beilstein J Org Chem. 2015 Nov 4;11:2097-104. doi: 10.3762/bjoc.11.226. eCollection 2015.

DOI:10.3762/bjoc.11.226
PMID:26664630
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4660996/
Abstract

A Chan-Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization.

摘要

Chan-Lam反应已被用于制备N-烯基-α,β-不饱和硝酮，其随后会发生热重排生成相应的三取代和四取代吡啶。本文讨论了这些转化反应的优化及适用范围。初步的机理实验表明反应途径涉及氧转移，随后是环化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/70125f7f6a8d/Beilstein_J_Org_Chem-11-2097-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/5150490d3279/Beilstein_J_Org_Chem-11-2097-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/0739ba8a4110/Beilstein_J_Org_Chem-11-2097-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/d702e45f5d10/Beilstein_J_Org_Chem-11-2097-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/70125f7f6a8d/Beilstein_J_Org_Chem-11-2097-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/5150490d3279/Beilstein_J_Org_Chem-11-2097-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/0739ba8a4110/Beilstein_J_Org_Chem-11-2097-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/d702e45f5d10/Beilstein_J_Org_Chem-11-2097-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/108d/4660996/70125f7f6a8d/Beilstein_J_Org_Chem-11-2097-g005.jpg

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本文引用的文献

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