Synthesis of oxadiazoles on solid support

被引:69
作者
Hébert, N [1 ]
Hannah, AL [1 ]
Sutton, SC [1 ]
机构
[1] Trega Biosci Inc, San Diego, CA 92121 USA
关键词
oxadiazoles; solid phase synthesis; combinatorial chemistry;
D O I
10.1016/S0040-4039(99)01826-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aliphatic and aromatic nitriles linked to solid support were converted to amide oximes, and cyclized to oxadiazoles using N-protected amino acid anhydrides. The amino protecting group was removed and the products acylated or sulfonylated on resin to provide combinatorial libraries of oxadiazoles. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8547 / 8550
页数:4
相关论文
共 12 条
[1]   Oxadiazoles as bioisosteric transformations of carboxylic functionalities .2. [J].
Andersen, KE ;
Lundt, BF ;
Jorgensen, AS ;
Braestrup, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (05) :417-425
[2]   A SIMPLIFIED PROCEDURE FOR PREPARING 3,5-DISUBSTITUTED-1,2,4-OXADIAZOLES BY REACTION OF AMIDOXIMES WITH ACYL CHLORIDES IN PYRIDINE SOLUTION [J].
CHIOU, S ;
SHINE, HJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :125-128
[3]   Novel 1,2,4-oxadiazoles as potent and selective histamine H-3 receptor antagonists [J].
Clitherow, JW ;
Beswick, P ;
Irving, WJ ;
Scopes, DIC ;
Barnes, JC ;
Clapham, J ;
Brown, JD ;
Evans, DJ ;
Hayes, AG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (07) :833-838
[4]   Parallel synthesis of 1,2,4-oxadiazoles using CDI activation [J].
Deegan, TL ;
Nitz, TJ ;
Cebzanov, D ;
Pufko, DE ;
Porco, JA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :209-212
[5]   OXADIAZOLES AS ESTER BIOISOSTERIC REPLACEMENTS IN COMPOUNDS RELATED TO DISOXARIL - ANTIRHINOVIRUS ACTIVITY [J].
DIANA, GD ;
VOLKOTS, DL ;
NITZ, TJ ;
BAILEY, TR ;
LONG, MA ;
VESCIO, N ;
ALDOUS, S ;
PEVEAR, DC ;
DUTKO, FJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2421-2436
[6]   New synthesis of SASRIN(TM) resin [J].
Katritzky, AR ;
Toader, D ;
Watson, K ;
Kiely, JS .
TETRAHEDRON LETTERS, 1997, 38 (45) :7849-7850
[7]   An improved oxadiazole synthesis using peptide coupling reagents [J].
Liang, GB ;
Feng, DD .
TETRAHEDRON LETTERS, 1996, 37 (37) :6627-6630
[8]   Synthesis and biological characterization of 1,4,5,6-tetrahydropyrimidine and 2-amino-3,4,5,6-tetrahydropyridine derivatives as selective m1 agonists [J].
Messer, WS ;
Abuh, YF ;
Liu, Y ;
Periyasamy, S ;
Ngur, DO ;
Edgar, MAN ;
ElAssadi, AA ;
Sbeih, S ;
Dunbar, PG ;
Roknich, S ;
Rho, T ;
Fang, Z ;
Ojo, B ;
Zhang, H ;
Huzl, JJ ;
Nagy, PI .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (08) :1230-1246
[9]   Preparation of acid-labile resins with halide linkers and their utility in solid phase organic synthesis [J].
Ngu, K ;
Patel, DV .
TETRAHEDRON LETTERS, 1997, 38 (06) :973-976
[10]   COMPARISON OF AZABICYCLIC ESTERS AND OXADIAZOLES AS LIGANDS FOR THE MUSCARINIC RECEPTOR [J].
ORLEK, BS ;
BLANEY, FE ;
BROWN, F ;
CLARK, MSG ;
HADLEY, MS ;
HATCHER, J ;
RILEY, GJ ;
ROSENBERG, HE ;
WADSWORTH, HJ ;
WYMAN, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2726-2735