Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones

被引:93
作者
Shaterian, Hamid Reza [1 ]
Oveisi, Ali Reza [1 ]
Honarmand, Moones [1 ]
机构
[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran
关键词
Al(H2PO4)3; 3-(2'benzothiazolo)-2; 3-dihydroqunazoline-4(1H)-ones; isatoic anhydride; solvent-free; ENVIRONMENTALLY FRIENDLY PREPARATION; PERCHLORIC-ACID HCLO4-SIO2; SILICA SULFURIC-ACID; ONE-POT; AMIDOALKYL NAPHTHOLS; REUSABLE CATALYST; SOLVENT-FREE; QUINAZOLINONE DERIVATIVES; TUBULIN POLYMERIZATION; HETEROGENEOUS CATALYST;
D O I
10.1080/00397910903064831
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, inexpensive, and heterogeneous catalyst, [Al(H2PO4)3], was applied in a three-component, one-pot cyclocondensation reaction of isatoic anhydride with primary amines (or ammonium salts) and aldehydes to afford the corresponding quinazolinone derivatives in excellent yields. Reactions occurred under thermal solvent-free conditions. It was found that this solid acidic catalyst could be easily recovered and reused for at least three cycles without any loss of activity.
引用
收藏
页码:1231 / 1242
页数:12
相关论文
共 38 条
[1]   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
[2]  
Armarego W.L. F., 1979, ADV HETEROCYCL CHEM, V24, P1
[3]   Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives [J].
Baghbanzadeh, M ;
Salehi, P ;
Dabiri, M ;
Kozeligarya, G .
SYNTHESIS-STUTTGART, 2006, (02) :344-348
[4]   Al(H2PO4)3:: An efficient catalyst for nitration of organic compounds with nitric acid [J].
Bharadwaj, Saitanya K. ;
Hussain, Sahid ;
Kar, Manoranjan ;
Chaudhuri, Mihir K. .
CATALYSIS COMMUNICATIONS, 2008, 9 (05) :919-923
[5]   2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES [J].
BONOLA, G ;
SIANESI, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (02) :329-&
[6]   Tyrosine kinase inhibitors .8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor [J].
Bridges, AJ ;
Zhou, H ;
Cody, DR ;
Rewcastle, GW ;
McMichael, A ;
Showalter, HDH ;
Fry, DW ;
Kraker, AJ ;
Denny, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) :267-276
[7]   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
[8]   Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid-water without additional catalyst [J].
Chen, Jiuxi ;
Su, Weike ;
Wu, Huayue ;
Liu, Miaochang ;
Jin, Can .
GREEN CHEMISTRY, 2007, 9 (09) :972-975
[9]   Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2•12H2O as a reusable catalyst in water and ethanol [J].
Dabiri, M ;
Salehi, P ;
Otokesh, S ;
Baghbanzadeh, M ;
Kozehgary, G ;
Mohammadi, AA .
TETRAHEDRON LETTERS, 2005, 46 (36) :6123-6126
[10]   Silica sulfuric acid:: An efficient reusable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water and under solvent-free conditions [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Baghbanzadeh, Mostafa ;
Zolfigol, Mohammad Ali ;
Agheb, Maria ;
Heydari, Sedigheh .
CATALYSIS COMMUNICATIONS, 2008, 9 (05) :785-788