Highly Efficient One-Pot Synthesis of 2-Substituted Quinazolines and 4H-Benzo[d][1,3]oxazines via Cross Dehydrogenative Coupling using Sodium Hypochlorite

被引:127
作者
Maheswari, C. Uma [1 ]
Kumar, G. Sathish [1 ]
Venkateshwar, M. [1 ]
Kumar, R. Arun [1 ]
Kantam, M. Lakshmi [1 ]
Reddy, K. Rajender [1 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500607, Andhra Pradesh, India
关键词
2-aryl-4H-benzo[d][1,3]oxazines; dehydrogenation; oxidation; quinazolines; sodium hypochlorite; TYROSINE KINASE INHIBITORS; DERIVATIVES; RECEPTOR; ALDEHYDES; AMINES; 4-ANILINOQUINAZOLINES; 2-ARYLBENZOXAZOLES; DISCOVERY; OXIDATION; QUINOLINE;
D O I
10.1002/adsc.200900715
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This communication describes a catalyst-free synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines using commericially available sodium hypochlorite as oxidant. Operational simplicity, mild reaction conditions and the ability to construct structurally diverse 2-quinazolines and 2-substituted 4H-benzo[d][1,3]oxazines by this method render it to be a practical alternative for the synthesis of these heterocycles.
引用
收藏
页码:341 / 346
页数:6
相关论文
共 46 条
[1]  
Armarego W.L.F., 1967, FUSED PYRIMIDINES 1
[2]   Studies leading to the identification of ZD1839 (Iressa™):: An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer [J].
Barker, AJ ;
Gibson, KH ;
Grundy, W ;
Godfrey, AA ;
Barlow, JJ ;
Healy, MP ;
Woodburn, JR ;
Ashton, SE ;
Curry, BJ ;
Scarlett, L ;
Henthorn, L ;
Richards, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (14) :1911-1914
[3]   Synthesis and biological activity of novel antibacterial quinazolines [J].
Bedi, PMS ;
Kumar, V ;
Mahajan, MP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5211-5213
[4]  
Bonomi P, 2003, EXPERT OPIN INV DRUG, V12, P1395, DOI 10.1517/eoid.12.8.1395.21769
[5]   Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines [J].
Chandrika, P. Mani ;
Yakaiah, T. ;
Rao, A. Raghu Ram ;
Narsaiah, B. ;
Reddy, N. Chakra ;
Sridhar, V. ;
Rao, J. Venkateshwara .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (04) :846-852
[6]   Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases - a solution-phase strategy for library synthesis [J].
Chang, JB ;
Zhao, K ;
Pan, SF .
TETRAHEDRON LETTERS, 2002, 43 (06) :951-954
[7]   Nucleosides XI.: Synthesis and antiviral evaluation of 5′-alkylthio-5′-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs [J].
Chien, TC ;
Chen, CS ;
Yu, FH ;
Chern, JW .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (12) :1422-1426
[8]   Synthesis of quinazolinones and quinazolines [J].
Connolly, DJ ;
Cusack, D ;
O'Sullivan, TP ;
Guiry, PJ .
TETRAHEDRON, 2005, 61 (43) :10153-10202
[9]  
Desai P, 1998, ASIAN J CHEM, V10, P615
[10]   Multidrug resistance mediated by the breast cancer resistance protein BCRP (ABCG2) [J].
Doyle, LA ;
Ross, DD .
ONCOGENE, 2003, 22 (47) :7340-7358