Concise synthesis of 2-amino-4(3H)-quinazolinones from simple (Hetero)aromatic amines

被引:36
作者
Zeghida, Walid [1 ]
Debray, Julien [1 ]
Chierici, Sabine [1 ]
Durny, Pascal [1 ]
Demeunynck, Martine [1 ]
机构
[1] Univ Grenoble 1, Dept Chim Mol, UMR 5250, F-38041 Grenoble, France
关键词
D O I
10.1021/jo7026883
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and simple method of preparation of 2-alkylaminoquinazolin-4-ones with fused heteroaromatic rings from easily accessible (hetero) aromatic amines is described. The method is very efficient, and the 2-alkylaminoquinazolinone derivatives are obtained in three steps without chromatographic purification. The key step is the ring closure of the N-protected guanidine intermediates by intramolecular Friedel-Craft's type substitution.
引用
收藏
页码:2473 / 2475
页数:3
相关论文
共 26 条
[1]   Synthesis and pharmacological investigation of novel 3-(3-methylphenyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents [J].
Alagarsamy, Veerachamy ;
Dhanabal, Kumarasamy ;
Parthiban, Periyasamy ;
Anjana, Gobi ;
Deepa, Govinhan ;
Murugesan, Balakrishnan ;
Rajkumar, Subramanian ;
Beevi, Abdulrahim Janath .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2007, 59 (05) :669-677
[2]   Synthesis and study of 4-hydroxymethyl-3-(alkylamino) acridines as models of a new class of DNA-intercalating-alkylating agents [J].
Charmantray, F ;
Duflos, A ;
Lhomme, J ;
Demeunynck, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :2962-2968
[3]   Studies on quinazolines and 1,2,4-benzothiadiazine 1,1-dioxides.: 8.: Synthesis and pharmacological evaluation of tricyclic fused quinazolines and 1,2,4-benzothiadiazine 1,1-dioxides as potential α1-adrenoceptor antagonists [J].
Chern, JW ;
Tao, PL ;
Wang, KC ;
Gutcait, A ;
Liu, SW ;
Yen, MH ;
Chien, SL ;
Rong, JK .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (17) :3128-3141
[4]   Synthesis and molecular structure of heterocyclic Troger's bases derived from C-amino heterocycles [J].
Cudero, J ;
Pardo, C ;
Ramos, M ;
GutierrezPuebla, E ;
Monge, A ;
Elguero, J .
TETRAHEDRON, 1997, 53 (06) :2233-2240
[5]  
Fixler N, 1998, HETEROCYCLES, V48, P755
[6]   Synthesis of substituted 2-amino-4-quinazolinones via ortho-fluorobenzoyl guanidines [J].
Fray, M. Jonathan ;
Mathias, John P. ;
Nichols, Carly L. ;
Po-Ba, Yvonne M. ;
Snow, Hayley .
TETRAHEDRON LETTERS, 2006, 47 (36) :6365-6368
[7]   Combinatorial synthesis of heterocycles:: Solid-phase synthesis of 2-amino-4(1H)-quinazolinone derivatives [J].
Gopalsamy, A ;
Yang, H .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (04) :378-381
[8]   SYNTHESIS OF 2-(ALKYLAMINO)-5,6 AND 2-(ALKYLAMINO)-6,7-DIHYDROXY-3,4-DIHYDROQUINAZOLINES AND EVALUATION AS POTENTIAL DOPAMINE AGONISTS [J].
GROSSO, JA ;
NICHOLS, DE ;
KOHLI, JD ;
GLOCK, D .
JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (06) :703-708
[9]   LIN-BENZOGUANINE - SYNTHESIS BY 2 INDEPENDENT METHODS [J].
KEYSER, GE ;
LEONARD, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3529-3532
[10]   Solid-phase synthesis of 2-aminoquinazolinone derivatives with two- and three-point diversity [J].
Kundu, B ;
Partani, P ;
Duggineni, S ;
Sawant, D .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (06) :909-915