A four-component Pfitzinger reaction: synthesis of 2-pyronylquinolin-4-carbamides
A four-component Pfitzinger reaction: synthesis of 2-pyronylquinolin-4-carbamides
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DOI：
10.1007/s11164-017-2885-8
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发表时间：
2017-08-01
影响因子：
3.3
通讯作者：
Moradi, Shahram
中科院分区：
文献类型：
--
作者：
Kalurazi, Sorayya Yaghoubi;Rad-Moghadam, Kurosh;Moradi, Shahram
通过靛红、乙酸铵、原乙酸三乙酯和4-羟基香豆素或4-羟基-6-甲基-2H-吡喃-2-酮之间的四组分顺序反应，开发了一种一锅法有效合成新型2-取代喹啉-4-甲酰胺。该方案是 Pfitzinger 喹啉合成的延伸，涉及 2H-吡喃酮环 3 位的前所未有的原位亚氨基乙酰化，随后依次进行靛红开环和重排环化反应。该产品是喹啉-4-甲酰胺和 4-羟基香豆素/4-羟基-6-甲基-2H-吡喃-2-酮杂环核的共价键对，其结构得到 NMR、IR 和质谱数据的支持。
A one-pot route was developed for efficient synthesis of novel 2-substituted quinolin-4-carboxamides via a four-component sequential reaction between isatins, ammonium acetate, triethyl orthoacetate, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2H-pyran-2-one. This protocol is an extension of Pfitzinger's quinoline synthesis and involves an unprecedented in situ iminoacetylation of 2H-pyrone ring at the 3-position followed sequentially by an isatin-ring-opening and a rearranged cyclization reaction. The products are covalently bound couples of quinolin-4-carboxamides and 4-hydroxycoumarin/4-hydroxy-6-methyl-2H-pyran-2-one heterocyclic nuclei with structures that are supported by their NMR, IR, and mass spectral data.