A CONVENIENT SYNTHESIS OF BRIDGED AZATRICYCLIC ANHYDRIDES

被引:19
作者
CANONNE, P
AKSSIRA, M
DAHDOUH, A
KASMI, H
BOUMZEBRA, M
机构
[1] UNIV ABDELMALEK ESSAADI,FAC SCI,DEPT CHIM,CHIM ORGAN LAB,BP 2121,TETOUAN,MOROCCO
[2] UNIV LAVAL,DEPT COMPREHENS CANC,QUEBEC CITY G1K 7P4,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4020(01)86298-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bridged N-protected beta-amino acids have been regioselectively prepared from the corresponding bicyclic monoesters. The subsequent cyclisation by thionyl chloride produced the desired bridged azatricyclic anhydrides which are versatile substrates for the synthesis of dipeptides; they are also converted into oxathymine and oxauracil by a thermal [4 + 2] cycloreversion.
引用
收藏
页码:1985 / 1992
页数:8
相关论文
共 30 条
[1]   NOVEL ROUTE TO SOME BIOLOGICALLY IMPORTANT COMPOUNDS STARTING WITH A COMMON CHIRAL, BICYCLIC, FUSED LACTONE - ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE AND 2 ANTITHROMBOTICS [J].
ARAI, Y ;
KAWANAMI, S ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :2969-2975
[2]  
BERNATH G, Patent No. 2643384
[3]   STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].
BLOCH, R ;
GUIBEJAMPEL, E ;
GIRARD, C .
TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090
[4]   SPIROCYCLIZATION OF 1-(ORTHO-AMINOPHENYL)CYCLOALKANOLS AND 1-(2'-AMINO-3'-PYRIDINYL)CYCLOALKANOLS [J].
CANONNE, P ;
BOULANGER, R ;
CHANTEGREL, B .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :113-117
[5]   STUDY OF THE REACTION OF PRIMARY ALKYLMAGNESIUMS AND ARYLMAGNESIUMS WITH BRIDGED TRICYCLIC ANHYDRIDES [J].
CANONNE, P ;
AKSSIRA, M ;
FYTAS, G .
TETRAHEDRON, 1984, 40 (10) :1809-1815
[6]   THE IMPORTANCE OF THE PRESENCE OF OXYGEN IN THE 7-POSITION IN THE REACTIONS OF SECONDARY ALKYLMAGNESIUM COMPOUNDS WITH BRIDGED TRICYCLIC ANHYDRIDES [J].
CANONNE, P ;
AKSSIRA, M ;
LEMAY, G .
TETRAHEDRON LETTERS, 1982, 23 (37) :3785-3788
[7]  
CANONNE P, 1988, TETRAHEDRON, V44, P2903
[8]   REACTIONS OF ALPHA,OMEGA-BIS(BROMOMAGNESIO)ALKANES WITH HETEROCYCLIC ANHYDRIDES - A NOVEL SYNTHESIS OF 5-MEMBERED AND 6-MEMBERED 1-(OMEGA-AMINOPHENYL)CYCLOALKANOLS AND 1-(2'-AMINO-3'-PYRIDINYL)CYCLOALKANOLS [J].
CANONNE, P ;
BOULANGER, R ;
CHANTEGREL, B .
TETRAHEDRON, 1987, 43 (04) :663-668
[9]   NOVEL SYNTHESIS OF 5-MEMBERED AND 6-MEMBERED SPIRO GAMMA-LACTONES IN RIGID BICYCLIC SYSTEMS [J].
CANONNE, P ;
BELANGER, D ;
LEMAY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3953-3959
[10]   A FACILE AND GENERAL-ROUTE TO 4-SUBSTITUTED-2 BUTENOLIDES [J].
CANONNE, P ;
AKSSIRA, M ;
LEMAY, G .
TETRAHEDRON LETTERS, 1981, 22 (28) :2611-2614