A convenient synthesis of chiral 1,2,4-oxadiazoles from N-protected (α-aminoacyl)benzotriazoles

被引:61
作者
Katritzky, AR [1 ]
Shestopalov, AA [1 ]
Suzuki, K [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
关键词
chiral 1,2,4-oxadiazole; N-aminoacylbenzotriazole; N-acylbenzotriazole; benzotriazole methodology;
D O I
10.3998/ark.5550190.0006.705
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,4-Oxadiazoles (4a-k, 6a-c, 7a-d, and 11a-f) derived from chiral alpha-amino acids were synthesized in 70-94% yields via a fast and easy procedure under mild conditions. They were shown to be at least 97% enantiomerically pure by HPLC and NMR.
引用
收藏
页码:36 / 55
页数:20
相关论文
共 51 条
[1]   OXADIAZOLES AS BIOISOSTERIC TRANSFORMATIONS OF CARBOXYLIC FUNCTIONALITIES .1. [J].
ANDERSEN, KE ;
JORGENSEN, AS ;
BRAESTRUP, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (05) :393-399
[2]   Investigation of bioisosters of the growth hormone secretagogue L-692,429. [J].
Ankersen, M ;
Peschke, B ;
Hansen, BS ;
Hansen, TK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (10) :1293-1298
[3]   NONQUATERNARY CHOLINESTERASE REACTIVATORS .3. 3(5)-SUBSTITUTED 1,2,4-OXADIAZOL-5(3)-ALDOXIMES AND 1,2,4-OXADIAZOLE-5(3)-THIOCARBOHYDROXIMATES AS REACTIVATORS OF ORGANOPHOSPHONATE-INHIBITED EEL AND HUMAN ACETYLCHOLINESTERASE INVITRO [J].
BEDFORD, CD ;
HOWD, RA ;
DAILEY, OD ;
MILLER, A ;
NOLEN, HW ;
KENLEY, RA ;
KERN, JR ;
WINTERLE, JS .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2174-2183
[4]   PREPARATION OF STILBENYL DERIVATIVES OF 1,2,4-OXADIAZOLES [J].
BERGER, H ;
SIEGRIST, AE .
HELVETICA CHIMICA ACTA, 1979, 62 (05) :1411-1428
[5]   SYNTHESIS OF 1,2,4-OXADIAZOLE-DERIVED, 1,3,4-OXADIAZOLE-DERIVED, AND 1,2,4-TRIAZOLE-DERIVED DIPEPTIDOMIMETICS [J].
BORG, S ;
ESTENNEBOUHTOU, G ;
LUTHMAN, K ;
CSOREGH, I ;
HESSELINK, W ;
HACKSELL, U .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3112-3120
[6]   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
[7]   'One-pot' synthesis of chiral N-protected α-amino acid-derived 1,2,4-oxadiazoles [J].
Braga, AL ;
Lüdtke, DS ;
Alberto, EE ;
Dornelles, L ;
Filho, WAS ;
Corbellini, VA ;
Rosa, DM ;
Schwab, RS .
SYNTHESIS-STUTTGART, 2004, (10) :1589-1594
[8]   Structure-activity relationships of a novel class of Src SH2 inhibitors [J].
Buchanan, JL ;
Vu, CB ;
Merry, TJ ;
Corpuz, EG ;
Pradeepan, SG ;
Mani, UN ;
Yang, M ;
Plake, HR ;
Varkhedkar, VM ;
Lynch, BA ;
MacNeil, IA ;
Loiacono, KA ;
Tiong, CL ;
Holt, DA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2359-2364
[9]   HETEROCYCLIC PHOTOREARRANGEMENTS - PHOTOCHEMICAL BEHAVIOR OF SOME 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES IN METHANOL AT 254 NM [J].
BUSCEMI, S ;
CICERO, MG ;
VIVONA, N ;
CARONNA, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) :931-935
[10]   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