期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 1, 页码 1037-1052出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02292
关键词
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资金
- Russian Science Foundation (RSF) [20-74-10121]
- Russian Science Foundation [20-74-10121] Funding Source: Russian Science Foundation
A new three-component reaction has been discovered, which can synthesize compounds with specific structure under mild conditions and high functional group tolerance, selectively functionalizing pyridines, and the reaction mechanism involves a rare [4+2] cycloaddition step.
A new three-component reaction leading to 1-alpha-(pyridyl-2-[1,2,4]triazolyl)-2-alkyl-ethanones has been discovered while studying the reactivity of monosubstituted 3,3-difluorocyclopropenes in an inverse electronic demand Diels-Alder (IEDDA) cycloaddition-cycloreversion sequence with s-tetrazines. The reaction involving the above-mentioned reactants and (benzo)pyridine as a third component results in a complex transformation proceeding in mild conditions in a stoichiometric ratio of reactants and has high functional group tolerance (phenols, amides, ethers, carboxylic acids, ketones, and acrylic esters). As a result, simple pyridines are selectively functionalized at the alpha-position in good isolated yields. The reaction mechanism includes a rare azaphilic [4 + 2]-cycloaddition step between s-tetrazine and intermediate 1-hydroxyindolizine, suggested after byproduct identification and tracked with a deuterium label. To date, it is only the third known example of skewed azaphilic cycloaddition of tetrazine. The reaction is truly three-component and cannot be effectively performed stepwise.
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