NEW SYNTHESIS OF (+/-)-2-PIPERAZINECARBOXYLIC ACID

被引：8

作者：

MEROUR, JY

COADOU, JY

机构：

[1] Laboratoire de chimie bioorganique et analytique, associé au CNRS, Université d'Orléans, 45067 Orléans

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 22期

关键词：

SCHMIDT REARRANGEMENT; FAVORSKII REARRANGEMENT; 4-PIPERIDONE; DIAZEPINONE; (+/-)-2-PIPERAZINECARBOXYLIC ACID;

D O I：

10.1016/S0040-4039(00)74356-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-2-Piperazinecarboxylic acid is prepared from N-carbethoxy-4-piperidone by a Schmidt rearrangement followed by bromation of the lactam; then a Favorskii rearrangement on the monobromolactam intermediate afforded the desired product.

引用

页码：2469 / 2470

页数：2

共 10 条

[1] SYNTHESIS AND NMDA ANTAGONISTIC PROPERTIES OF THE ENANTIOMERS OF 4-(3-PHOSPHONOPROPYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP) AND OF THE UNSATURATED ANALOG (E)-4-(3-PHOSPHONOPROP-2-ENYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP-ENE)
AEBISCHER, B
FREY, P
HAERTER, HP
HERRLING, PL
MUELLER, W
OLVERMAN, HJ
WATKINS, JC
[J]. HELVETICA CHIMICA ACTA, 1989, 72 (05) : 1043 - 1051
[2] BACH F. L., 1955, JOUR AMER CHEM SOC, V77, P6049, DOI 10.1021/ja01627a075
[3] NEW PREPARATIONS OF THE N-METHYL-D-ASPARTATE RECEPTOR ANTAGONIST, 4-(3-PHOSPHONOPROPYL)-2-PIPERAZINECARBOXYLIC ACID (CPP)
BIGGE, CF
HAYS, SJ
NOVAK, PM
DRUMMOND, JT
JOHNSON, G
BOBOVSKI, TP
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5193 - 5196
[4] CPP, A NEW POTENT AND SELECTIVE NMDA ANTAGONIST - DEPRESSION OF CENTRAL NEURON RESPONSES, AFFINITY FOR [H-3] D-AP5 BINDING-SITES ON BRAIN MEMBRANES AND ANTICONVULSANT ACTIVITY
DAVIES, J
EVANS, RH
HERRLING, PL
JONES, AW
OLVERMAN, HJ
POOK, P
WATKINS, JC
[J]. BRAIN RESEARCH, 1986, 382 (01) : 169 - 173
[5] THE PREPARATION AND AMMONOLYSIS OF ALPHA-HALOGEN DERIVATIVES OF EPSILON-CAPROLACTAM - A NEW SYNTHESIS OF LYSINE
FRANCIS, WC
THORNTON, JR
WERNER, JC
HOPKINS, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (23) : 6238 - 6244
[6] NEW AND VERSATILE APPROACHES TO THE SYNTHESIS OF CPP-RELATED COMPETITIVE NMDA ANTAGONISTS - PRELIMINARY STRUCTURE-ACTIVITY-RELATIONSHIPS AND PHARMACOLOGICAL EVALUATION
HAYS, SJ
BIGGE, CF
NOVAK, PM
DRUMMOND, JT
BOBOVSKI, TP
RICE, MJ
JOHNSON, G
BRAHCE, LJ
COUGHENOUR, LL
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) : 2916 - 2924
[7] JOHNSON G, 1989, ANNU REP MED CHEM, V24, P41
[8] EXCITATORY AMINO-ACID NEUROTRANSMISSION
JOHNSON, RL
KOERNER, JF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) : 2057 - 2066
[9] UNTERSUCHUNGEN UBER SYNTHETISCHE ARZNEIMITTEL .10. UBER C-SUBSTITUIERTE PIPERAZINDERIVATE
JUCKER, E
RISSI, E
[J]. HELVETICA CHIMICA ACTA, 1962, 45 (07) : 2383 - &
[10] INFLUENCE OF PSEUDOALLYLIC STRAIN ON THE CONFORMATIONAL PREFERENCE OF 4-METHYL-4-PHENYLPIPECOLIC ACID-DERIVATIVES
SUGG, EE
GRIFFIN, JF
PORTOGHESE, PS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5032 - 5037

← 1 →