Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles,Synthesis

当前位置： X-MOL 学术 › Synthesis › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles
Synthesis ( IF 2.2 ) Pub Date : 2020-03-12 , DOI: 10.1055/s-0039-1707987
Ivan S. Kondratov _{1,

2} , Oleksandr O. Grygorenko _{1,

3} , Oleksandr O. Stepaniuk _{1,

3} , Tymofii V. Rudenko _{1,

3} , Bohdan V. Vashchenko _{1,

3} , Vitalii O. Matvienko ₁ , Andrey A. Tolmachev _{1,

3}

Affiliation

An efficient approach to the preparation of pyridine carboxylates fused with 5- or 6-membered heteroaromatic rings is described. The method relied on the Combes-type condensation of the low-molecular-weight β-alkoxyvinyl glyoxylates as CCC bis-electrophiles and with heteroaromatic amines as NCC binucleophiles. In most experiments, β-alkoxyvinyl glyoxylates without additional substituent at the β position led to the corresponding α-pyridine carboxylates (67–87% yield). In the case of β-methyl-substituted derivative, γ-pyridine carboxylates were obtained in 84–99% yield. It was found that regioselectivity of the condensation could be efficiently tuned by changing conditions, such as solvents and acidic additives (HOAc, DMSO or HCl–1,4-dioxane).

中文翻译：

β-烷氧基乙烯基乙醛酸酯与氨基杂环化合物的反应合成吡啶吡啶羧酸酯

描述了一种制备与5或6元杂芳族环稠合的吡啶羧酸酯的有效方法。该方法依赖于低分子量β-烷氧基乙烯基乙醛酸酯作为CCC双亲电子试剂和杂芳族胺作为NCC双亲核试剂的Combes型缩合反应。在大多数实验中，在β位置上没有其他取代基的β-烷氧基乙烯基乙醛酸酯会生成相应的α-吡啶羧酸酯（67-87％的收率）。对于β-甲基取代的衍生物，以84–99％的产率获得γ-吡啶羧酸盐。发现可以通过改变条件（例如溶剂和酸性添加剂（HOAc，DMSO或HCl–1,4-二恶烷））有效地调节缩合的区域选择性。

更新日期：2020-03-12

点击分享查看原文

点击收藏

阅读更多本刊最新论文