Barium manganate in microwave-assisted oxidation reactions: synthesis of lactones by oxidative cyclization of diols

被引:35
作者
Bagley, Mark C. [1 ]
Lin, Zhifan [1 ]
Phillips, David J. [1 ]
Graham, Andrew E. [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales
基金
英国工程与自然科学研究理事会;
关键词
WERNER-SYNDROME CELLS; HIGHLY EFFICIENT SYNTHESIS; SELECTIVE MONOACYLATION; SILICA-GEL; HEATING ELEMENTS; ALCOHOLS; DEHYDROGENATION; DIOXIDE; DESYMMETRIZATION; ELECTROOXIDATION;
D O I
10.1016/j.tetlet.2009.09.117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Microwave irradiation of a range of diols at 150 degrees C in acetonitrile in the presence of three equivalents of barium manganate facilitates a novel tandem oxidation/heterocyclocondensation to give the corresponding lactone, including both small and medium ring lactones, in only one hour and in high yield without the need for chromatographic purification. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6823 / 6825
页数:3
相关论文
共 54 条
[1]  
AMAIKE M, 1995, LIEBIGS ANN, P1451
[2]   STRUCTURAL AND CONFORMATIONAL STUDIES ON SESQUITERPENOID ESTERS FROM LASERPITIUM-HALLERI CRANTZ SUBSP HALLERI [J].
APPENDINO, G ;
VALLE, MG ;
GARIBOLDI, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1363-1372
[3]   Microwave-assisted synthesis of 5-aminopyrazol-4-yl ketones and the p38MAPK inhibitor RO3201195 for study in Werner syndrome cells [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Murziani, Paola G. S. ;
Rokicki, Michal J. ;
Kipling, David .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (13) :3745-3748
[4]  
Bagley MC, 2006, TOP HETEROCYCLIC CHE, V1, P31
[5]   Rapid synthesis of VX-745: p38 MAP kinase inhibition in Werner syndrome cells [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Rokicki, Michal J. ;
Kipling, David .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (18) :5107-5110
[6]   Regioselective microwave-assisted synthesis of substituted pyrazoles from ethynyl ketones [J].
Bagley, Mark C. ;
Lubinu, M. Caterina ;
Mason, Christopher .
SYNLETT, 2007, (05) :704-708
[7]   Microwave-assisted synthesis of N-pyrazole ureas and the p38α inhibitor BIRB 796 for study into accelerated cell ageing [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Widdowson, Caroline S. ;
Kipling, David .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4158-4164
[8]   Rapid Ullmann-type synthesis of aryl sulfides using a copper(I) catalyst and ligand under microwave irradiation [J].
Bagley, Mark C. ;
Dix, Matthew C. ;
Fusillo, Vincenzo .
TETRAHEDRON LETTERS, 2009, 50 (26) :3661-3664
[9]   Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide [J].
Bagley, MC ;
Lubinu, MC .
SYNTHESIS-STUTTGART, 2006, (08) :1283-1288
[10]   A simple continuous flow microwave reactor [J].
Bagley, MC ;
Jenkins, RL ;
Lubinu, MC ;
Mason, C ;
Wood, R .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :7003-7006