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Cu(II)–Glucose: Sustainable Catalyst for the Synthesis of Quinazolinones in a Biomass-Derived Solvent 2-MethylTHF and Application for the Synthesis of Diproqualone
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-10-15 00:00:00 , DOI: 10.1021/acssuschemeng.8b02940 Abhishek V. Dubey 1 , A. Vijay Kumar 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-10-15 00:00:00 , DOI: 10.1021/acssuschemeng.8b02940 Abhishek V. Dubey 1 , A. Vijay Kumar 1
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An efficient method for the synthesis of quinazolinones by a domino cross-coupling reaction of 2-halobenzoic acids and amidines is demonstrated for the first time using a copper–glucose combination as an inexpensive catalytic system in a biomass-derived green solvent 2-methylTHF. Here, glucose plays a dual role, both as a reducing agent generating the low-valent copper ions from cupric precursors and as a chelating agent of the generated low-valent copper species, thereby impeding their deactivation. A wide variety of quinazolinones were synthesized in good to excellent yields. Notably, the activation of less reactive 2-bromo/chlorobenzoic acids by the catalyst not only advocates the efficiency of the developed protocol but also the broad substrate scope. Moreover, the developed methodology was successfully applied to the synthesis of the drug molecule diproqualone. The UV–vis spectrophotometric titration study of cupric and cuprous salts with glucose showed evidence of glucose playing the role as a ligand, thus it may act as a stabilizing agent for the low valent copper species formed in the reaction. The use of inexpensive and air stable cupric salts along with glucose for the synthesis of quinazolinones in a green solvent makes this a benign and sustainable method.
中文翻译：
铜（II）-葡萄糖：在生物质衍生的2-甲基THF中合成喹唑啉酮类的可持续催化剂及其在双丙戊酮合成中的应用
通过2-卤代苯甲酸和am的多米诺骨牌交叉偶联反应，首次证明了铜-葡萄糖组合作为廉价的催化体系在生物质衍生的绿色溶剂2-甲基THF中催化合成喹唑啉酮的有效方法。在此，葡萄糖起着双重作用，既是从铜前体产生低价铜离子的还原剂，又是所产生的低价铜物质的螯合剂，从而阻碍了它们的失活。合成了多种喹唑啉酮类化合物，收率良好至优异。值得注意的是，催化剂对反应性较低的2-溴/氯苯甲酸的活化不仅提倡了所开发方案的效率，而且提倡了广泛的底物范围。而且，所开发的方法已成功地应用于药物分子双丙孕酮的合成。葡萄糖对铜和亚铜盐的紫外可见分光光度滴定研究表明，葡萄糖起着配体的作用，因此它可以作为反应中形成的低价铜种类的稳定剂。在绿色溶剂中使用廉价且空气稳定的铜盐与葡萄糖一起合成喹唑啉酮，使该方法成为一种良性且可持续的方法。
更新日期：2018-10-15
中文翻译：
铜（II）-葡萄糖：在生物质衍生的2-甲基THF中合成喹唑啉酮类的可持续催化剂及其在双丙戊酮合成中的应用
通过2-卤代苯甲酸和am的多米诺骨牌交叉偶联反应，首次证明了铜-葡萄糖组合作为廉价的催化体系在生物质衍生的绿色溶剂2-甲基THF中催化合成喹唑啉酮的有效方法。在此，葡萄糖起着双重作用，既是从铜前体产生低价铜离子的还原剂，又是所产生的低价铜物质的螯合剂，从而阻碍了它们的失活。合成了多种喹唑啉酮类化合物，收率良好至优异。值得注意的是，催化剂对反应性较低的2-溴/氯苯甲酸的活化不仅提倡了所开发方案的效率，而且提倡了广泛的底物范围。而且，所开发的方法已成功地应用于药物分子双丙孕酮的合成。葡萄糖对铜和亚铜盐的紫外可见分光光度滴定研究表明，葡萄糖起着配体的作用，因此它可以作为反应中形成的低价铜种类的稳定剂。在绿色溶剂中使用廉价且空气稳定的铜盐与葡萄糖一起合成喹唑啉酮，使该方法成为一种良性且可持续的方法。
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