Selective Synthesis of Highly Functionalized Bicyclic Pyridinone and 1,3-Oxazinane Derivatives

被引：7

作者：

Cui, Shi-Sheng ^{[1
]}

Huang, Rong ^{[1
]}

Luo, Da-Yun ^{[1
]}

Yan, Sheng-Jiao ^{[1
]}

Lin, Jun ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 24期

基金：

中国国家自然科学基金;

关键词：

Synthetic methods; Heterocycles; Fused-ring systems; Regioselectivity; Ketene aminals; HETEROCYCLIC KETENE AMINALS; RING-FUSED; 2-PYRIDONES; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; SPIROOXINDOLE DERIVATIVES; BIOLOGICAL EVALUATION; PYRROLE DERIVATIVES; SOLVENT-FREE; INHIBITORS;

D O I：

10.1002/ejoc.201700283

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic pyridinone and 1,3-oxazinane derivatives (i.e., 3 and 4) have been synthesized by the regioselective condensation reaction of heterocyclic ketene aminals (HKAs) and either ethyl 2-cyano-3,3-bis(methylthio)acrylate or 2-[bis(methylthio) methylene]malononitrile in xylene at reflux. Pyridinone compounds 3 were efficiently obtained under catalyst-free conditions, whereas 1,3-oxazinane derivatives 4 were obtained by adding Cs2CO3 to the reaction mixture under the same conditions. The reactions afforded the products in excellent yields by using inexpensive starting materials and a convenient workup process.

引用

页码：3442 / 3450

页数：9

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