Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold,Journal of Heterocyclic Chemistry

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Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2019-12-30 , DOI: 10.1002/jhet.3832
Ali Keivanloo ₁ , Mohammad Bakherad ₁ , Lotfollah Mokhtarei ₁

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Water soluble sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate ligand was used successfully for the preparation of 1,2,3‐triazoles pharmacophore linked‐quinazolinone scaffold. The reaction of ethyl 4‐oxo‐3,4‐dihydroquinazoline‐2‐carboxylate and related amide compounds with propargyl bromide afforded ethyl 4‐oxo‐3‐(prop‐2‐yn‐1‐yl)‐3,4‐dihydroquinazoline‐2‐carboxylate and its amide derivatives. The reaction of propargylated compounds with azides catalyzed by copper (II) salt, in the presence of Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate as a ligand in water produced novel 1,2,3‐triazole pharmacophore linked‐quinazolinone‐4‐one scaffold with high‐to‐excellent yields. The ligand assisted in the click reaction and reduced loading of copper salt to 2 mol%. Simplicity, short reaction times, use of water as green solvent, and low catalyst loading are the main advantages of this procedure.

中文翻译：

4-氨基-5-羟基-7-磺基萘-2-磺酸钠是水中点击反应的有效配体：1,2,3-三唑药效团连接的喹唑啉酮骨架的合成

水溶性4-氨基-5-羟基-7-磺基萘-2-磺酸钠配体已成功用于制备1,2,3-三唑类药效团连接的喹唑啉酮骨架。4-氧代-3-3,4-二氢喹唑啉-2-羧酸乙酯和相关的酰胺化合物与炔丙基溴的反应得到乙基4-氧代-3-（prop-2-yn-1-基）-3-，4-二氢喹唑啉2-羧酸盐及其酰胺衍生物。在水中存在4-氨基-5-羟基-7-磺基萘-2-磺酸钠作为配体的情况下，铜（II）催化的炔丙基化化合物与叠氮化物的反应产生了新的1,2,3-三唑药效基团链接到的喹唑啉酮-4支架，产量高至出色。所述配体有助于点击反应并将铜盐的负载降低至2mol％。简单，反应时间短，使用水作为绿色溶剂，

更新日期：2019-12-31

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