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

被引：85

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

页码：209 / 212

页数：4

共 13 条

[1] 1,2,4-OXADIAZOLE DERIVATIVES OF PHENYLALANINE - POTENTIAL INHIBITORS OF SUBSTANCE-P ENDOPEPTIDASE
BORG, S
LUTHMAN, K
NYBERG, F
TERENIUS, L
HACKSELL, U
[J]. 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
CHEN, CY
SENANAYAKE, CH
BILL, TJ
LARSEN, RD
VERHOEVEN, TR
REIDER, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3738 - 3741
[3] 1,2,4-OXADIAZOLES
CLAPP, LB
[J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 : 65 - 116
[4] OXADIAZOLES AS ESTER BIOISOSTERIC REPLACEMENTS IN COMPOUNDS RELATED TO DISOXARIL - ANTIRHINOVIRUS ACTIVITY
DIANA, GD
VOLKOTS, DL
NITZ, TJ
BAILEY, TR
LONG, MA
VESCIO, N
ALDOUS, S
PEVEAR, DC
DUTKO, FJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) : 2421 - 2436
[5] CHEMISTRY OF AMIDOXIMES AND RELATED COMPOUNDS
ELOY, F
LENAERS, R
[J]. CHEMICAL REVIEWS, 1962, 62 (02) : 155 - &
[6] An improved oxadiazole synthesis using peptide coupling reagents
Liang, GB
Feng, DD
[J]. 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
Macor, JE
Ordway, T
Smith, RL
Verhoest, PR
Mack, RA
[J]. 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
OOI, NS
WILSON, DA
[J]. 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
ORLEK, BS
BLANEY, FE
BROWN, F
CLARK, MSG
HADLEY, MS
HATCHER, J
RILEY, GJ
ROSENBERG, HE
WADSWORTH, HJ
WYMAN, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) : 2726 - 2735
[10] TETRAHYDROPYRIDYLOXADIAZOLES - SEMIRIGID MUSCARINIC LIGANDS
SHOWELL, GA
GIBBONS, TL
KNEEN, CO
MACLEOD, AM
MERCHANT, K
SAUNDERS, J
FREEDMAN, SB
PATEL, S
BAKER, R
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) : 1086 - 1094

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