Copper(I) reactions in N-heterocycle synthesis:: efficient preparation of substituted pyrrolidinones

被引：41

作者：

Davies, DT

Kapur, N

Parsons, AF ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] SmithKline Beecham Pharmaceut, Dept Med Chem, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

copper; copper compounds; radicals; radical reactions; cyclisation; enamides;

D O I：

10.1016/S0040-4039(99)01805-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of halo-enamides with copper(I) chloride in boiling toluene has been shown to produce unsaturated pyrrolidinones in excellent yield (81-94%). Both di- and trichloroamide precursors can be used to form dienes via an initial 5-endo-trig radical cyclisation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8615 / 8618

页数：4

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共 12 条

[1] Tandem radical cyclisation of enamides mediated by tin hydride; pyrrolizidinone or indolizidinone ring formation [J].

Baker, SR ;

Burton, KI ;

Parsons, AF ;

Pons, JF ;

Wilson, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04) :427-436

[2] LIGAND EFFECTS IN THE RHODIUM(II)-CATALYZED REACTIONS OF ALPHA-DIAZOAMIDES - OXINDOLE FORMATION IS PROMOTED BY THE USE OF RHODIUM(II) PERFLUOROCARBOXAMIDE CATALYSTS [J].

BROWN, DS ;

ELLIOTT, MC ;

MOODY, CJ ;

MOWLEM, TJ ;

MARINO, JP ;

PADWA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2447-2455

[3] β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations.: A concise construction of the mesembrine skeleton [J].

Cassayre, J ;

Quiclet-Sire, B ;

Saunier, JB ;

Zard, SZ .

TETRAHEDRON, 1998, 54 (07) :1029-1040

[4] Efficient room temperature copper(I) mediated 5-endo radical cyclisations [J].

Clark, AJ ;

Dell, CP ;

Ellard, JM ;

Hunt, NA ;

McDonagh, JP .

TETRAHEDRON LETTERS, 1999, 40 (49) :8619-8623

[5] Manganese(III) reactions in N-heterocycle synthesis:: The preparation of substituted pyrrolidinones [J].

Davies, DT ;

Kapur, N ;

Parsons, AF .

TETRAHEDRON LETTERS, 1998, 39 (24) :4397-4400

[6] The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to γ-lactams.: Application to the stereoselective synthesis of pilolactam. [J].

Ghelfi, F ;

Bellesia, F ;

Forti, L ;

Ghirardini, G ;

Grandi, R ;

Libertini, E ;

Montemaggi, MC ;

Pagnoni, UM ;

Pinetti, A ;

De Buyck, L ;

Parsons, AF .

TETRAHEDRON, 1999, 55 (18) :5839-5852

[7] A radical cyclisation approach to pyroglutamates [J].

Goodall, K ;

Parsons, AF .

TETRAHEDRON, 1996, 52 (19) :6739-6758

[8] TRANSITION METAL-PROMOTED FREE-RADICAL REACTIONS IN ORGANIC-SYNTHESIS - THE FORMATION OF CARBON-CARBON BONDS [J].

IQBAL, J ;

BHATIA, B ;

NAYYAR, NK .

CHEMICAL REVIEWS, 1994, 94 (02) :519-564

[9] Effect of temperature on 5-endo- and 4-exo-trig radical cyclizations of N-vinylic α-halo amides [J].

Ishibashi, H ;

Higuchi, M ;

Ohba, M ;

Ikeda, M .

TETRAHEDRON LETTERS, 1998, 39 (1-2) :75-78

[10] Copper-catalyzed facile carbon-carbon bond forming reactions at the α-position of α,α,γ-trichlorinated γ-lactams [J].

Iwamatsu, S ;

Kondo, H ;

Matsubara, K ;

Nagashima, H .

TETRAHEDRON, 1999, 55 (06) :1687-1706