Synthesis of Quinazolinones from Alcohols via Laccase-Mediated Tandem Oxidation

被引:36
|
作者
Heidary, Marjan [1 ]
Khoobi, Mehdi [2 ,3 ]
Ghasemi, Sabrieh [1 ]
Habibi, Zohreh [1 ]
Faramarzi, Mohammad Ali [4 ,5 ]
机构
[1] Shahid Beheshti Univ, Dept Pure Chem, Fac Chem, Tehran, Iran
[2] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran 14176, Iran
[3] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran 14176, Iran
[4] Univ Tehran Med Sci, Dept Pharmaceut Biotechnol, Fac Pharm, Tehran 14176, Iran
[5] Univ Tehran Med Sci, Biotechnol Res Ctr, Tehran 14176, Iran
关键词
biocatalysis; laccase; oxidation; oxidoreductases; quinazolinones; ONE-POT SYNTHESIS; ASCOMYCETE PARACONIOTHYRIUM-VARIABILE; CATALYZED OXIDATION; ENZYME LACCASE; EXTRACELLULAR LACCASE; GREEN CHEMISTRY; 4(3H)-QUINAZOLINONES; ANALOGS; DERIVATIVES; HETEROCYCLES;
D O I
10.1002/adsc.201400103
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This paper describes the synthesis of quinazolinones via a tandem reaction using the laccase-mediator system under mild conditions. The procedure involved the laccase-catalyzed oxidation of alcohols to the corresponding aldehydes, followed by cyclocondensation with isatoic anhydride and a number of amines to afford 2,3-dihydroquinazolin-4(1H)-ones, which were further oxidized to quinazolinones in useful yields. The use of an enzyme as the catalyst, O2 as an environmentally friendly oxidant, and a citrate buffer as the green solvent represents a novel and efficient approach for the one-pot synthesis of quinazolinones.
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页码:1789 / 1794
页数:6
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