The accelerated development of an optimized synthesis of 1,2,4-oxadiazoles: application of microwave irradiation and statistical design of experiments

被引:68
作者
Evans, MD
Ring, J
Schoen, A
Bell, A
Edwards, P
Berthelot, D
Nicewonger, R
Baldino, CM
机构
[1] ArQule Inc, Dept Chem, Woburn, MA 01801 USA
[2] Pfizer Ltd, Global Res & Dev, Lib Design & Prod Grp, Sandwich Labs, Sandwich CT13 9NJ, Kent, England
关键词
oxadiazole; microwave; design of experiments; amidoxime; optimization;
D O I
10.1016/j.tetlet.2003.10.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report the development of an optimized microwave-assisted synthesis of 1,2,4-oxadiazoles. The chemistry development process was significantly accelerated by employing a statistical software package (MODDE 6.0(TM)) to guide in the optimization of the reaction conditions. The resulting optimized reaction conditions were then utilized in the synthesis of a focused library of 1,2,4-oxadiazoles. (C) 2003 Published by Elsevier Ltd.
引用
收藏
页码:9337 / 9341
页数:5
相关论文
共 13 条
[1]   Design, synthesis, and evaluation of Phe-Gly mimetics: Heterocyclic building blocks for pseudopeptides [J].
Borg, S ;
Vollinga, RC ;
Labarre, M ;
Payza, K ;
Terenius, L ;
Luthman, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4331-4342
[2]   3-ARYL-2-(3'-SUBSTITUTED-1',2',4'-OXADIAZOL-5'-YL)TROPANE ANALOGS OF COCAINE - AFFINITIES AT THE COCAINE BINDING-SITE AT THE DOPAMINE, SEROTONIN, AND NOREPINEPHRINE TRANSPORTERS [J].
CARROLL, FI ;
GRAY, JL ;
ABRAHAM, P ;
KUZEMKO, MA ;
LEWIN, AH ;
BOJA, JW ;
KUHAR, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2886-2890
[3]   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
[4]   CHEMISTRY OF AMIDOXIMES AND RELATED COMPOUNDS [J].
ELOY, F ;
LENAERS, R .
CHEMICAL REVIEWS, 1962, 62 (02) :155-&
[5]   Microwave assisted organic synthesis -: a review [J].
Lidström, P ;
Tierney, J ;
Wathey, B ;
Westman, J .
TETRAHEDRON, 2001, 57 (45) :9225-9283
[6]   Potent, selective human β3 adrenergic receptor agonists containing a substituted indoline-5-sulfonamide pharmacophore [J].
Mathvink, RJ ;
Barritta, AM ;
Candelore, MR ;
Cascieri, MA ;
Deng, LP ;
Tota, L ;
Strader, CD ;
Wyvratt, MJ ;
Fisher, MH ;
Weber, AE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) :1869-1874
[7]   OXIDATION OF HYDRAZONES BY LEAD-DIOXIDE - NEW SYNTHESES OF 1,3,4-OXADIAZOLES AND DERIVATIVES OF 4-AMINO-1,2,4-TRIAZOLE-5-ONE [J].
MILCENT, R ;
BARBIER, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (01) :77-80
[8]   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
[9]   SYNTHESIS OF OXADIAZOLES AND OXAZOLES WITH THIOPHENE SUBSTITUENT [J].
OUSSAID, B ;
MOEINI, L ;
GARRIGUES, B ;
VILLEMIN, D .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 85 (1-4) :23-30
[10]   IMPROVED SYNTHESIS OF OXADIAZOLES UNDER MICROWAVE IRRADIATION [J].
OUSSAID, B ;
MOEINI, L ;
MARTIN, B ;
VILLEMIN, D ;
GARRIGUES, B .
SYNTHETIC COMMUNICATIONS, 1995, 25 (10) :1451-1459