A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones

被引:58
作者
Zhan, Dan [1 ]
Li, Tianbin [1 ]
Wei, Haidong [1 ]
Weng, Wen [2 ]
Ghandi, Khashayar [3 ]
Zeng, Qingle [1 ]
机构
[1] Chengdu Univ Technol, Inst Green Catalysis & Synth, State Key Lab Geohazard Prevent & Geoenvironm Pro, Coll Mat & Chem & Chem Engn, Chengdu 610059, Peoples R China
[2] Zhangzhou Normal Univ, Dept Chem & Environm Sci, Zhangzhou 363000, Peoples R China
[3] Mt Allison Univ, Dept Chem & Biochem, Sackville, NB E0A 3C0, Canada
关键词
ONE-POT SYNTHESIS; ENANTIOSELECTIVE SULFOXIDATION; EFFICIENT SYNTHESIS; IONIC LIQUID; DERIVATIVES; QUINAZOLINONE; OXIDATION; AGENTS; CHEMISTRY; ALDEHYDES;
D O I
10.1039/c3ra41370e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper describes the synthesis of 2-substituted and 2,3-disubstituted 4(3H)-quinazolinones via a tandem reaction involving anthranilamides and aromatic aldehydes catalyzed by 3 mol% CuO powder under air atmosphere. This new method has several advantages: it uses recyclable and cheap CuO powder as the catalyst and air as the green oxidant, water is the only byproduct, and the solvent is recycled. It is easy to run, has a high atom economy and good to excellent yields. A mechanism for the CuO-catalyzed synthesis of the 4(3H)-quinazolinones is proposed.
引用
收藏
页码:9325 / 9329
页数:5
相关论文
共 45 条
[1]   A novel method for the synthesis of 4(3H)-quinazolinones [J].
Abdel-Jalil, RJ ;
Voelter, W ;
Saeed, M .
TETRAHEDRON LETTERS, 2004, 45 (17) :3475-3476
[2]  
Adib M., 2011, SYNLETT, V2012, P85
[3]   PALLADIUM COMPLEX-CATALYZED INTERMOLECULAR REDUCTIVE N-HETEROCYCLIZATION - NOVEL SYNTHESIS OF QUINAZOLINE DERIVATIVES FROM 2-NITROBENZALDEHYDE OR 2-NITROPHENYL KETONES WITH FORMAMIDE [J].
AKAZOME, M ;
YAMAMOTO, J ;
KONDO, T ;
WATANABE, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 494 (1-2) :229-233
[4]   Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents [J].
Alagarsamy, V. ;
Solomon, V. Raja ;
Dhanabal, K. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :235-241
[5]   Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones [J].
Alagarsamy, Veerachamy ;
Pathak, Urvishbhai S. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3457-3462
[6]  
Armarego W.L. F., 1979, ADV HETEROCYCL CHEM, V24, P1
[7]  
Benaglia M., 2009, RECOVERABLE RECYCLAB
[8]  
Bogert M.T., 1902, J AM CHEM SOC, V24, P1031, DOI [10.1021/ja02025a001, DOI 10.1021/JA02025A001]
[9]   Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones [J].
Chen, Jiuxi ;
Wu, Dengze ;
He, Fei ;
Liu, Miaochang ;
Wu, Huayue ;
Ding, Jinchang ;
Su, Weike .
TETRAHEDRON LETTERS, 2008, 49 (23) :3814-3818
[10]   A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Bahramnejad, Mahboobeh ;
Alizadeh, Mohsen .
MONATSHEFTE FUR CHEMIE, 2010, 141 (08) :877-881