Manganese(III) reactions in N-heterocycle synthesis:: The preparation of substituted pyrrolidinones

被引:28
作者
Davies, DT
Kapur, N
Parsons, AF [1 ]
机构
[1] Univ York, Dept Chem, York YO1 5DD, N Yorkshire, England
[2] SmithKline Beecham Pharmaceut, Dept Med Chem, Harlow CM19 5AW, Essex, England
关键词
manganese and compounds; radicals and radical reactions; cyclisation; enamides;
D O I
10.1016/S0040-4039(98)00746-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of various N-acyl enamines with manganese(III) acetate in boiling methanol has been explored. This was shown to produce functionalised pyrrolidinones via a 5-endo-trig radical cyclisation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4397 / 4400
页数:4
相关论文
共 11 条
[1]  
CARDILLO B, 1995, SYNLETT, P1159
[2]   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
[3]  
CHOI JK, 1988, B KOR CHEM SOC, V9, P129
[4]   MN(III) - PROMOTED CYCLIZATION OF ENAMIDES - AN OXIDATIVE RADICAL APPROACH TO BETA-LACTAMS [J].
DANNIBALE, A ;
RESTA, S ;
TROGOLO, C .
TETRAHEDRON LETTERS, 1995, 36 (49) :9039-9042
[5]   Preparation of diethyl 2-alkoxymethyl-, 2-phenylselenomethyl- and 2-phenylthiomethylmalonate [J].
Delepine, JL ;
Pecquet, P ;
Betton, M ;
Huet, F .
SYNTHETIC COMMUNICATIONS, 1996, 26 (15) :2819-2829
[6]   A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid [J].
Galeazzi, R ;
Mobbili, G ;
Orena, M .
TETRAHEDRON, 1996, 52 (03) :1069-1084
[7]   A radical cyclisation approach to pyroglutamates [J].
Goodall, K ;
Parsons, AF .
TETRAHEDRON, 1996, 52 (19) :6739-6758
[8]   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
[9]   FORMATION OF 5-MEMBERED LACTAMS BY 5-ENDO-TRIGONAL RADICAL CYCLIZATIONS OF 2-CHLORO-N-(CYCLOALK-1-ENYL)ACETAMIDES - NEW SYNTHESIS OF ERYTHRINANE SKELETON [J].
SATO, T ;
NAKAMURA, N ;
IKEDA, K ;
OKADA, M ;
ISHIBASHI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18) :2399-2407
[10]   Manganese(III)-based oxidative free-radical cyclizations [J].
Snider, BB .
CHEMICAL REVIEWS, 1996, 96 (01) :339-363