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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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