Synthesis of 1-hydroxypyrazole glycine derivatives

被引:14
作者
Calí, P [1 ]
Begtrup, M [1 ]
机构
[1] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark
关键词
arylglycine; amino acid; 1-hydroxypyrazole; imino malonate;
D O I
10.1016/S0040-4020(02)00021-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel alpha-amino acids containing the 1-hydroxypyrazole ring has been prepared by addition of organomagnesium or organolithium intermediates to diethyl N-Boc-iminomalonate as an electrophilic glycine equivalent. Electrophiles, aryl and heteroaryl substituents were introduced in the pyrazole ring. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:1595 / 1605
页数:11
相关论文
共 28 条
[1]  
[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[2]   Regioselective introduction of electrophiles in the 4-position of 1-hydroxypyrazole via bromine-lithium exchange [J].
Balle, T ;
Vedso, P ;
Begtrup, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5366-5370
[3]   Structure-activity relationships for a series of phenylglycine derivatives acting at metabotropic glutamate receptors (mGluRs) [J].
Bedingfield, JS ;
Kemp, MC ;
Jane, DE ;
Tse, HW ;
Roberts, PJ ;
Watkins, JC .
BRITISH JOURNAL OF PHARMACOLOGY, 1995, 116 (08) :3323-3329
[4]   THERMOLYSIS OF ORTHO-NITROPHENYLLITHIUM [J].
BUCK, P ;
GLEITER, R ;
KOBRICH, G .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (05) :1431-&
[5]  
Calí P, 2002, SYNTHESIS-STUTTGART, P63
[6]   RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650
[7]   Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships [J].
Falch, E ;
Brehm, L ;
Mikkelsen, I ;
Johansen, TN ;
Skjaerbaek, N ;
Nielsen, B ;
Stensbol, TB ;
Ebert, B ;
Krogsgaard-Larsen, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) :2513-2523
[8]   Synthesis of 4-substituted 1-(benzyloxy)pyrazoles via iodine-magnesium exchange of 1-(benzyloxy)-4-iodopyrazole [J].
Felding, J ;
Kristensen, J ;
Bjerregaard, T ;
Sander, L ;
Vedso, P ;
Begtrup, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :4196-4198
[9]  
FLYNN EH, 1972, PENICILLINS CEPHALOS
[10]  
HO TL, 1985, TETRAHEDRON, V41, P1