Cycloadditions of 3,4-dihydro-2H-pyrrole 1-oxide to methylene-gamma-butyrolactones

被引:11
作者
AlonsoPerarnau, D [1 ]
deMarch, P [1 ]
elArrad, M [1 ]
Figueredo, M [1 ]
Font, J [1 ]
Parella, T [1 ]
机构
[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,BELLATERRA 08193,BARCELONA,SPAIN
关键词
D O I
10.1016/S0040-4020(97)00987-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the reactions of nitrone 1 with several methylene-gamma-butyrolactones 2-5 we have isolated and identified in all the cases the corresponding [3+2] cycloadducts. In all the adducts the oxygen atom of the dipole has linked to the more substituted carbon atom of the exocyclic double bond of the lactone. For lactone 5 the exocyclic double bond has shown higher reactivity than the endocyclic. Herein three new heterocyclic skeletons are reported. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:14763 / 14772
页数:10
相关论文
共 36 条
[1]   PERACID INDUCED RING-OPENING OF ISOXAZOLIDINES - A MECHANISTIC STUDY [J].
ALI, SA ;
WAZEER, MIM .
TETRAHEDRON LETTERS, 1992, 33 (22) :3219-3222
[2]  
ALI SA, 1990, TETRAHEDRON, V46, P7207
[3]   THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF 1,3-DIPOLAR CYCLO-ADDITION OF A CYCLIC NITRONE [J].
ALI, SA ;
WAZEER, MIM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :597-605
[4]   DIELS-ALDER REACTIONS OF PROTOANEMONIN WITH HETEROSUBSTITUTED DIENES - SYNTHESIS OF POLYFUNCTIONAL OXASPIRO[4.5]DECANES [J].
ALONSO, D ;
FONT, J ;
ORTUNO, RM ;
DANGELO, J ;
GUINGANT, A ;
BOIS, C .
TETRAHEDRON, 1991, 47 (30) :5895-5900
[5]   GENERAL-SYNTHESIS OF 1-OXASPIRO[4.5]DECAN-2-ONES AND 1-OXASPIRO[4.5]DECANES FROM 5-METHYLENE-2(5H)-FURANONE [J].
ALONSO, D ;
FONT, J ;
ORTUNO, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5567-5572
[6]   CYCLOADDITION REACTIONS OF 3,4-DIHYDRO-2H-PYRROLE 1-OXIDE WITH ALPHA,BETA-UNSATURATED LACTONES [J].
ALONSOPERARNAU, D ;
DEMARCH, P ;
FIGUEREDO, M ;
FONT, J ;
SORIA, A .
TETRAHEDRON, 1993, 49 (20) :4267-4274
[7]   CYCLOADDITION OF C,N-DIARYLNITRONES TO 2-BUTENOLIDE - SYNTHESIS OF 2,3,6,6A-TETRAHYDROFURO[3,4-D]ISOXAZOL-4(3AH)-ONE [J].
BANERJI, A ;
BASU, S .
TETRAHEDRON, 1992, 48 (16) :3335-3344
[8]  
BASKARAN S, 1995, J CHEM RES-S, P308
[9]   STUDIES ON STRUCTURALLY SIMPLE BUTENOLIDES .5. REACTIONS OF PROTOANEMONIN WITH PIPERIDINE AND C-NUCLEOPHILES - A GENERAL-APPROACH TO ITS BEHAVIOR AS ELECTROPHILIC ACCEPTOR [J].
BIGORRA, J ;
FONT, J ;
JAIME, C ;
ORTUNO, RM ;
SANCHEZFERRANDO, F .
TETRAHEDRON, 1985, 41 (23) :5577-5587
[10]  
BUSQUE F, 1995, HETEROCYCLES, V40, P387