A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations

被引:24
作者
Ayaz, Muhammad [1 ]
Dietrich, Justin [1 ]
Hulme, Christopher [1 ,2 ]
机构
[1] Univ Arizona, Coll Pharm, Tucson, AZ 85721 USA
[2] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA
关键词
Petasis reaction; Multicomponent reaction; Quinoxaline; Intramolecular cyclization; Microwave; BIOLOGICAL EVALUATION; DERIVATIVES; ACID; ANTIBACTERIAL; ANTIFUNGAL; INHIBITORS; DISCOVERY; DESIGN;
D O I
10.1016/j.tetlet.2011.06.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Letter reveals an innovative and facile procedure to prepare quinoxalines in two synthetic steps. The microwave assisted Petasis reaction is followed by the acid mediated unmasking of an internal amino nucleophile, cyclodehydration and oxidation to give collections of quinoxalines in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4821 / 4823
页数:3
相关论文
共 33 条
[1]   Synthesis of certain substituted quinoxalines as antimicrobial agents (part II) [J].
Badran, MM ;
Abouzid, KAM ;
Hussein, MHM .
ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (02) :107-113
[2]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[3]   SYNTHETIC ANTIMALARIALS .39. DIALKYLAMINOALKYLAMINOQUINOXALINES [J].
CROWTHER, AF ;
CURD, FHS ;
DAVEY, DG ;
STACEY, GJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (MAY) :1260-1271
[4]  
Dailey S, 2001, J MATER CHEM, V11, P2238, DOI 10.1039/b104674h
[5]   Concise two-step solution phase syntheses of four novel dihydroquinazoline scaffolds [J].
Dietrich, Justin ;
Kaiser, Christine ;
Meurice, Nathalie ;
Hulme, Christopher .
TETRAHEDRON LETTERS, 2010, 51 (30) :3951-3955
[6]  
El-Gendy Adel A., 1995, Archives of Pharmacal Research (Seoul), V18, P44, DOI 10.1007/BF02976507
[7]  
El-Hawash SA, 1999, PHARMAZIE, V54, P808
[8]  
Ganapaty S, 2007, INDIAN J HETEROCY CH, V16, P283
[9]   Synthesis of novel cyclic α-amino acid derivatives via a one-pot sequential Petasis reaction/palladium catalysed process [J].
Grigg, R ;
Sridharan, V ;
Thayaparan, A .
TETRAHEDRON LETTERS, 2003, 44 (50) :9017-9019
[10]   Concise preparation of novel tricyclic chemotypes: fused hydantoin-benzodiazepines [J].
Gunawan, Steven ;
Nichol, Gary S. ;
Chappeta, Shashi ;
Dietrich, Justin ;
Hulme, Christopher .
TETRAHEDRON LETTERS, 2010, 51 (36) :4689-4692