Intramolecular Cyclization of Alkynylheteroaromatic Substrates Bearing a Tethered Cyano Group: A Strategy for Accessing Fused Pyridoheterocycles
Intramolecular Cyclization of Alkynylheteroaromatic Substrates Bearing a Tethered Cyano Group: A Strategy for Accessing Fused Pyridoheterocycles
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DOI：
10.1021/acs.joc.3c01411
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发表时间：
2023-08-17
影响因子：
3.6
通讯作者：
Hoye，Thomas R.
中科院分区：
文献类型：
--
作者：
Kraemer，Niklas;Eason，Erin M.;Hoye，Thomas R.
杂环底物含有共轭的炔和侧基腈被证明在整个tetradehydro-Diels-桤木反应中环化，得到其中初始杂环带有新稠合的吡啶环的产物。碱促进的炔到其异构丙二烯的互变异构化允许该过程在环境温度下发生。密度泛函理论的研究支持了对整体结果的许多机械解释。
Heterocyclic substrates containing a conjugated alkyne and a pendant nitrile were shown to cyclize in an overall tetradehydro-Diels–Alder reaction to give products in which the initial heterocycle bears a newly fused pyridine ring. Base-promoted tautomerization of the alkyne to its isomeric allene allows this process to occur at ambient temperature. DFT studies support many of the mechanistic interpretations of the overall results.