Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods

D T  Davies; N  Kapur; A F  Parsons

Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods

D T Davies, N Kapur, A F Parsons

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	3941-3949
Number of pages	9
Journal	Tetrahedron
Volume	56
Issue number	24
Publication status	Published - 9 Jun 2000

Keywords

manganese and compounds
copper and compounds
cyclisation
enamides
SUBSTITUTED PYRROLIDINONES
TIN HYDRIDE
SECONDARY AMIDES
GAMMA-LACTAMS
CYCLIZATION
PYROGLUTAMATES
TEMPERATURE
5-ENDO-TRIG
4-EXO-TRIG
CATALYSTS

Cite this

@article{3db51499e12a4b5b979b4a315cd8293e,

title = "Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods",

abstract = "Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "manganese and compounds, copper and compounds, cyclisation, enamides, SUBSTITUTED PYRROLIDINONES, TIN HYDRIDE, SECONDARY AMIDES, GAMMA-LACTAMS, CYCLIZATION, PYROGLUTAMATES, TEMPERATURE, 5-ENDO-TRIG, 4-EXO-TRIG, CATALYSTS",

author = "Davies, {D T} and N Kapur and Parsons, {A F}",

year = "2000",

month = jun,

day = "9",

language = "English",

volume = "56",

pages = "3941--3949",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "24",

}

TY - JOUR

T1 - Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods

AU - Davies, D T

AU - Kapur, N

AU - Parsons, A F

PY - 2000/6/9

Y1 - 2000/6/9

N2 - Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - manganese and compounds

KW - copper and compounds

KW - cyclisation

KW - enamides

KW - SUBSTITUTED PYRROLIDINONES

KW - TIN HYDRIDE

KW - SECONDARY AMIDES

KW - GAMMA-LACTAMS

KW - CYCLIZATION

KW - PYROGLUTAMATES

KW - TEMPERATURE

KW - 5-ENDO-TRIG

KW - 4-EXO-TRIG

KW - CATALYSTS

M3 - Article

SN - 0040-4020

VL - 56

SP - 3941

EP - 3949

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -