Isoxazolinoisoquinoline heterocycles via solid-phase Reissert and Suzuki reactions

被引:61
作者
Lorsbach, BA [1 ]
Bagdanoff, JT [1 ]
Miller, RB [1 ]
Kurth, MJ [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
D O I
10.1021/jo9720142
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A traceless solid-phase synthesis strategy has been developed that delivers novel isoxazolinoisoquinoline heterocycles. The process consists of solid-phase Reissert formation (isoquinoline --> I), Suzuki coupling lithiation, and subsequent C1-alkylation (I --> II), and exo-olefin selective 1,3-dipolar nitrile oxide cycloaddition followed by Reissert; hydrolysis (II --> III) to liberate the targeted heterocycle.
引用
收藏
页码:2244 / 2250
页数:7
相关论文
共 47 条
[11]   CYCLOADDITION REACTIONS OF NITRILE OXIDES WITH ALKENES [J].
EASTON, CJ ;
HUGHES, CMM ;
SAVAGE, GP ;
SIMPSON, GW .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 60, 1994, 60 :261-327
[12]   Design, synthesis, and evaluation of small-molecule libraries [J].
Ellman, JA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :132-143
[13]   BIARYL SYNTHESIS VIA SUZUKI COUPLING ON A SOLID SUPPORT [J].
FRENETTE, R ;
FRIESEN, RW .
TETRAHEDRON LETTERS, 1994, 35 (49) :9177-9180
[14]  
GIBSON HW, 1991, POLYM COMMUN, V32, P324
[15]  
GIBSON HW, 1988, AM CHEM SOC POLYM PR, V29, P154
[16]   Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery [J].
Gordon, EM ;
Gallop, MA ;
Patel, DV .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :144-154
[17]   ISOXAZOLINE DERIVATIVES AS POTENTIAL INHIBITORS OF THE PROTEOLYTIC-ENZYMES HUMAN-LEUKOCYTE ELASTASE, CATHEPSIN-G AND PROTEINASE-3 - A STRUCTURE-ACTIVITY RELATIONSHIP STUDY [J].
GROUTAS, WC ;
VENKATARAMAN, R ;
CHONG, LS ;
YODER, JE ;
EPP, JB ;
STANGA, MA ;
KIM, EH .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (02) :125-128
[18]  
GUILE JW, 1996, 211 NAT M AM CHEM SO
[19]   Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction [J].
Han, YX ;
Walker, SD ;
Young, RN .
TETRAHEDRON LETTERS, 1996, 37 (16) :2703-2706
[20]  
Jones G., 1982, QUINOLINES 2, P353