Nucleophilic opening of the aziridine ring in 1-alkyl-1-azoniatricyclo[2.2.1.026]heptanes

被引：6

作者：

Bulanov, MN ^{[1
]}

Sosonyuk, SE ^{[1
]}

Zyk, NV ^{[1
]}

Zefirov, NS ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Fac Chem, Moscow 119992, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 39卷 / 03期

基金：

俄罗斯基础研究基金会;

关键词：

Bromide; Organic Chemistry; Heptane; Aziridine; Aziridine Ring;

D O I：

10.1023/A:1025554100991

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Opening of the aziridine ring in 3-bromo-1-alkyl-1-azoniatricyclo[2.2.1.0(2,6)]heptane bromides by the action of various nucleophiles leads to formation of the corresponding 6-substituted 2-alkyl-2-azabicyclo-[2.2.1]heptanes.

引用

页码：415 / 421

页数：7

共 11 条

[1] SYNTHESIS, PHYSICOCHEMICAL AND CONFORMATIONAL PROPERTIES OF (3R,4R)-3-(3-CYCLOPROPYL-1,2,4-OXADIAZOL-5-YL)-1-AZABICYCLO[2.2.1]HEPTANE, A NOVEL M(1) SELECTIVE MUSCARINIC PARTIAL AGONIST [J].

BAKER, R ;

SHOWELL, GA ;

STREET, LJ ;

SAUNDERS, J ;

HOOGSTEEN, K ;

FREEDMAN, SB ;

HARGREAVES, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (11) :817-819

[2] STRUCTURAL ELUCIDATION OF DISUBSTITUTED NORTRICYCLENES THROUGH VICINAL C-13, H-1 COUPLING-CONSTANTS [J].

GRIDNEV, ID ;

LESHCHEVA, IF ;

SERGEYEV, NM ;

CHERTKOV, VA .

MAGNETIC RESONANCE IN CHEMISTRY, 1992, 30 (09) :817-822

[3] CERTAIN METAL DERIVATIVES OF 2,4-PENTANEDIONE [J].

HATCH, LF ;

SUTHERLAND, G .

JOURNAL OF ORGANIC CHEMISTRY, 1948, 13 (02) :249-253

[4] REACTIONS OF ETHYL 2-ACETYL-2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-CARBOXYLATE AND 4-ACETYLAMINO-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE WITH SOME ELECTROPHILES [J].

HURSTHOUSE, MB ;

MALIK, KMA ;

HIBBS, DE ;

ROBERTS, SM ;

SEAGO, AJH ;

SIK, V ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (19) :2419-2425

[5]

NAGAEV VM, 1997, IZV AKAD NAUK SER KH, P1649

[6] New prolyl endopeptidase inhibitors: In vitro and in vivo activities of azabicyclo[2.2.2] octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives [J].

Portevin, B ;

Benoist, A ;

Remond, G ;

Herve, Y ;

Vincent, M ;

Lepagnol, J ;

DeNanteuil, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (12) :2379-2391

[7]

SOSONYUK SE, 2002, IZV ROSS AKAD NAUK K, P1157

[8] EPIBATIDINE - A NOVEL (CHLOROPYRIDYL)AZABICYCLOHEPTANE WITH POTENT ANALGESIC ACTIVITY FROM AN ECUADORIAN POISON FROG [J].

SPANDE, TF ;

GARRAFFO, HM ;

EDWARDS, MW ;

YEH, HJC ;

PANNELL, L ;

DALY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) :3475-3478

[9] PREPARATION AND REACTIONS OF TRIPHENYLTINLITHIUM [J].

TAMBORSKI, C ;

SOLOSKI, EJ ;

FORD, FE .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (01) :181-&

[10]

WALDMANN H, 1989, LIEBIGS ANN CHEM, P231

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