Synthesis of 1-arylmethyl-2-(2-cyanoethyl)aziridines and their rearrangement into novel 2-(Aminomethyl)cyclopropanecarbonitriles

被引：36

作者：

D'hooghe, Matthias ^{[1
]}

Vervisch, Karel ^{[1
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 19期

关键词：

D O I：

10.1021/jo701302a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 1-Arylmethyl-2-(bromomethyl)aziridines were transformed into novel 2-(2-cyanoethyl)aziridines upon treatment with alpha-lithiated trimethylsilylacetonitrile in THF in an efficient and straightforward approach. The latter aziridines underwent ring opening by reaction with benzyl bromide in acetonitrile, affording 5-amino-4-bromopentanenitriles through a regiospecific ring opening of intermediate aziridinium salts by bromide. Further elaboration of these gamma-bromonitriles resulted in the synthesis of novel 2-[N,N-bis(arylmethyl)amiriomethyl]cyclopropanecarbonitriles in high yields by means of a 1,3-cyclization protocol upon treatment with KOtBu in THF.

引用

页码：7329 / 7332

页数：4

共 50 条

[1]

[Anonymous], 2007, Patent, Patent No. [WO 2007028789, 2007028789]

[2]

Barbier F, 2002, SYNLETT, P811

[3] CATALYTIC CYCLOPROPANATION WITH TRANSITION-METAL SALTS OF SOLUBLE POLYETHYLENE CARBOXYLATES [J].

BERGBREITER, DE ;

MORVANT, M ;

CHEN, B .

TETRAHEDRON LETTERS, 1991, 32 (24) :2731-2734

[4] CYCLOADDITION REACTIONS OF AZIDES WITH ELECTRON-POOR OLEFINS - ISOMERIZATION AND THERMOLYSIS OF RESULTING DELTA-2-TRIAZOLINES [J].

BROECKX, W ;

OVERBERG, N ;

SAMYN, C ;

SMETS, G ;

LABBE, G .

TETRAHEDRON, 1971, 27 (15) :3527-+

[5] Charged residues at the 2′ position of human GABAc ρ1 receptors invert ion selectivity and influence open state probability [J].

Carland, JE ;

Moorhouse, AJ ;

Barry, PH ;

Johnston, GAR ;

Chebib, M .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (52) :54153-54160

[6] Mutations of the 2′ proline in the M2 domain of the human GABAC ρ1 subunit alter agonist responses [J].

Carland, JE ;

Moore, AM ;

Hanrahan, JR ;

Mewett, KN ;

Duke, RK ;

Johnston, GAR ;

Chebib, M .

NEUROPHARMACOLOGY, 2004, 46 (06) :770-781

[7] Enantiomers of cis-constrained and flexible 2-substituted GABA analogues exert opposite effects at recombinant GABAC receptors [J].

Crittenden, DL ;

Park, A ;

Qiu, J ;

Silverman, RB ;

Duke, RK ;

Johnston, GAR ;

Jordan, MJT ;

Chebib, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (02) :447-455

[8] Synthesis of spacered cyclopropyl nucleoside analogues as potential antiviral agents [J].

Csuk, R ;

Kern, A .

TETRAHEDRON, 1999, 55 (28) :8409-8422

[9] Regio- and stereospecific ring opening of 1,1-dialkyl-2-(aryloxymethyl)aziridinium salts by bromide [J].

D'hooghe, M ;

Van Speybroeck, V ;

Waroquier, M ;

De Kimpe, N .

CHEMICAL COMMUNICATIONS, 2006, (14) :1554-1556

[10] A new approach towards 2-amino-1-aryloxy-3-methoxypropanes from 1-arylmethyl-2-(bromomethyl)aziridines [J].

D'hooghe, M ;

Waterinckx, A ;

Vanlangendonck, T ;

De Kimpe, N .

TETRAHEDRON, 2006, 62 (10) :2295-2303

← 1 2 3 4 5 →