Parallel synthesis of 1,2,4-oxadiazoles using CDI activation

被引：86

作者：

Deegan, TL

Nitz, TJ

Cebzanov, D

Pufko, DE

Porco, JA

机构：

[1] Argonaut Technol, San Carlos, CA 94070 USA

[2] Viropharma Inc, Exton, PA 19341 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 02期

关键词：

D O I：

10.1016/S0960-894X(98)00712-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

1,2,4-Oxadiazoles have been prepared in parallel using 1,1'-carbonyldiimidazole (CDI) as a reagent for both formation and cyclodehydration of O-acyl benzamidoximes. The use of CDI facilitates parallel purification of the oxadiazole products by simple liquid-liquid extraction and filtration. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：209 / 212

页数：4

相关论文

共 13 条

[1] 1,2,4-OXADIAZOLE DERIVATIVES OF PHENYLALANINE - POTENTIAL INHIBITORS OF SUBSTANCE-P ENDOPEPTIDASE [J].

BORG, S ;

LUTHMAN, K ;

NYBERG, F ;

TERENIUS, L ;

HACKSELL, U .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (10) :801-810

[2] 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

[3] 1,2,4-OXADIAZOLES [J].

CLAPP, LB .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 :65-116

[4] 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

[5] CHEMISTRY OF AMIDOXIMES AND RELATED COMPOUNDS [J].

ELOY, F ;

LENAERS, R .

CHEMICAL REVIEWS, 1962, 62 (02) :155-&

[6] An improved oxadiazole synthesis using peptide coupling reagents [J].

Liang, GB ;

Feng, DD .

TETRAHEDRON LETTERS, 1996, 37 (37) :6627-6630

[7] Synthesis and use of 5-vinyl-1,2,4-oxadiazoles as Michael acceptors. A rapid synthesis of the potent muscarinic agonist L-670,548 [J].

Macor, JE ;

Ordway, T ;

Smith, RL ;

Verhoest, PR ;

Mack, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3228-3229

[8] FORMATION AND THERMAL-REACTION OF O-(N-ACETYLBENZIMIDOYL)BENZAMIDOXIME - COMPARISON WITH THE FORMATION OF 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES FROM O-ACETYLARYLAMIDOXIMES AND O-AROYLACETAMIDOXIMES [J].

OOI, NS ;

WILSON, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (12) :1792-1799

[9] 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

[10] TETRAHYDROPYRIDYLOXADIAZOLES - SEMIRIGID MUSCARINIC LIGANDS [J].

SHOWELL, GA ;

GIBBONS, TL ;

KNEEN, CO ;

MACLEOD, AM ;

MERCHANT, K ;

SAUNDERS, J ;

FREEDMAN, SB ;

PATEL, S ;

BAKER, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1086-1094