NOVEL SPIRO CYCLIZATIONS OF N-ACYLIMINIUM IONS INVOLVING AN AROMATIC PI-NUCLEOPHILE

被引：26

作者：

BAILEY, PD

MORGAN, KM

SMITH, DI

VERNON, JM

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

[2] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND

[3] STERLING WINTHROP RES INST,DIV PHARMACEUT RES,DEPT CHEM DEV,ALNWICK NE66 2JH,NORTHD,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 38期

关键词：

D O I：

10.1016/0040-4039(94)88240-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several spiro 2-pyrrolidin-5-ones were obtained by a two-step procedure from N-substituted succinimides, involving spiro cyclisation of N-acyliminium ion intermediates in refluxing trifluoroacetic acid; in all cases cyclisation utilised a tethered aromatic pi-nucleophile, and ring-closure followed 5- or 6-exo-trig pathways.

引用

页码：7115 / 7118

页数：4

共 9 条

[1] EVANS DA, 1979, TETRAHEDRON LETT, P411
[2] ULTRASOUND ASSISTED PREPARATION OF ORGANOCERIUM REAGENTS
GREEVES, N
LYFORD, L
[J]. TETRAHEDRON LETTERS, 1992, 33 (33) : 4759 - 4760
[3] REGIOSELECTIVE FORMATION OF HYDROXY LACTAMS FROM PYRIDINE-2,3-DICARBOXIMIDES AND THEIR CYCLODEHYDRATION TO PYRIDO[2',3'-3,4]PYRROLO-FUSED HETEROCYCLIC-SYSTEMS
HITCHINGS, GJ
VERNON, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1757 - 1763
[4] REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE
IMAMOTO, T
TAKIYAMA, N
NAKAMURA, K
HATAJIMA, T
KAMIYA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4392 - 4398
[5] PANDEY PN, 1982, SYNTHESIS-STUTTGART, P877
[6] SCHOEMAKER HE, 1979, TETRAHEDRON LETT, P2437
[7] SCHOEMAKER HE, 1978, TETRAHEDRON LETT, P1515
[8] STEREOCONTROLLED SYNTHESIS OF FUNCTIONALIZED 1-AZASPIRANS - EFFICIENT SYNTHESIS OF PERHYDROHISTRIONICOTOXIN
SCHOEMAKER, HE
SPECKAMP, WN
[J]. TETRAHEDRON, 1980, 36 (07) : 951 - 958
[9] INTRAMOLECULAR AMIDOALKYLATIONS AT CARBON . SYNTHESIS OF HETEROCYCLIC AMINES
WINN, M
ZAUGG, HE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10) : 3779 - &

← 1 →