Solid-phase synthesis of linked heterocycles from a selenopolystyrene resin

被引:16
作者
Huang, Xian
Wang, Yu-Guang
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2007年 / 9卷 / 01期
关键词
D O I
10.1021/cc0600775
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A linked heterocycle library of isoxazoles, 1,2,3-triazoles, bicyclo[2.2.1]hepta-2,5-diene or 4-methylcyclohexa-1,3-diene and 1,2,4-oxadiazoles was prepared by solid-phase organic synthesis. Key steps on resin-bound selenium were electrophilic additions; 1,3-dipolar cycloaddition; Porco's two-step, one-pot condensation of amidoxime and carboxylate; and Diels-Alder reaction.
引用
收藏
页码:121 / 130
页数:10
相关论文
共 69 条
[1]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[2]   6,6′-Dibromo-4,4′-di(hexoxymethyl)-2,2′-bipyridine:: A new solubilizing building block for macromolecular and supramolecular applications [J].
Amb, Chad M. ;
Rasmussen, Seth C. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12) :4696-4699
[3]  
[Anonymous], 1988, NITRILE OXIDES NITRO
[4]   3,3′-bis(diphenylphosphino)-1,1′-disubstituted-2,2′-biindoles:: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters [J].
Benincori, T ;
Piccolo, O ;
Rizzo, S ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8340-8347
[5]   'One-pot' synthesis of chiral N-protected α-amino acid-derived 1,2,4-oxadiazoles [J].
Braga, AL ;
Lüdtke, DS ;
Alberto, EE ;
Dornelles, L ;
Filho, WAS ;
Corbellini, VA ;
Rosa, DM ;
Schwab, RS .
SYNTHESIS-STUTTGART, 2004, (10) :1589-1594
[6]   The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles [J].
Bräse, S ;
Gil, C ;
Knepper, K .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2415-2437
[7]   Palladium-catalysed reactions in solid phase organic synthesis [J].
Bräse, S ;
Kirchhoff, JH ;
Köbberling, J .
TETRAHEDRON, 2003, 59 (07) :885-939
[8]   STUDIES ON 1,2,3-TRIAZOLES .13. (PIPERAZINYLALKOXY)[1]BENZOPYRANO[2,3-D]-1,2,3-TRIAZOL-9(1H)-ONES WITH COMBINED H-1 ANTIHISTAMINE AND MAST-CELL STABILIZING PROPERTIES [J].
BUCKLE, DR ;
ROCKELL, CJM ;
SMITH, H ;
SPICER, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2262-2267
[9]  
Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis
[10]   IMPROVED FISCHER INDOLE REACTION FOR THE PREPARATION OF N,N-DIMETHYLTRYPTAMINES - SYNTHESIS OF L-695,894, A POTENT 5-HT1D RECEPTOR AGONIST [J].
CHEN, CY ;
SENANAYAKE, CH ;
BILL, TJ ;
LARSEN, RD ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3738-3741