Metal-catalysed radical cyclisations leading to N-heterocycles:: new approaches to gabapentin and pulchellalactam

被引：60
作者：
Bryans, JS
Chessum, NEA
Huther, N
Parsons, AF
Ghelfi, F
机构：
[1] Univ York, Dept Chem, Heslington YO10 5DD, N Yorkshire, England
[2] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy
[3] Pfizer Global Res & Dev, Sandwich YO10 9NJ, Kent, England
来源：
TETRAHEDRON | 2003年 / 59卷 / 33期
基金：
英国生物技术与生命科学研究理事会;
关键词：
amino acids cyclisations; nitrogen heterocycles; radical reactions; GAMMA-LACTAMS; BETA-LACTAMS; COPPER(I); ACID; REARRANGEMENT; ELABORATION; VERSATILE; HYDRIDE; REAGENT; 4-EXO;
D O I：
10.1016/S0040-4020(03)01030-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：6221 / 6231
页数：11
相关论文
共 44 条
[21]  
2-5
[22]   SIMPLE AND CONDENSED BETA-LACTAMS .9. ELABORATION OF THE 3-(1-HYDROXYETHYL) SIDE-CHAINS OF POTENTIAL INTERMEDIATES OF CARBAPENEM ANTIBIOTICS VIA THE 2-METHYL-1,3-DIOXOLAN-2-YL GROUP [J].
FETTER, J ;
LEMPERT, K ;
KAJTARPEREDY, M ;
SIMIG, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1135-1142
[23]  
Galeazzi R, 1997, TARG HETEROCYCL SYST, V1, P355
[24]   Synthesis of 5-methoxylated 3-pyrrolin-2-ones via the rearrangement of chlorinated pyrrolidin-2-ones [J].
Ghelfi, F ;
Stevens, CV ;
Laureyn, I ;
Van Meenen, E ;
Rogge, TM ;
De Buyck, L ;
Nikitin, KV ;
Grandi, R ;
Libertini, E ;
Pagnoni, UM ;
Schenetti, L .
TETRAHEDRON, 2003, 59 (08) :1147-1157
[25]   Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones [J].
Ghelfi, F ;
Ghirardini, G ;
Libertini, E ;
Forti, L ;
Pagnoni, UM .
TETRAHEDRON LETTERS, 1999, 40 (49) :8595-8597
[26]   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
[27]   N,N-(dimethylamino)-2-pyrrolidinones from the rearrangement of N-allyl-N′,N′-dimethyl-2,2-dichlorohydrazides promoted by CuCl-N,N,N′,N′-tetramethylethylendiamine [J].
Ghelfi, F ;
Parsons, AF .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6249-6253
[28]   NOVEL SYNTHESES OF GABAPENTIN VIA ADDITION OF HYDROCYANIC ACID TO CYCLOHEXYLIDENEMALONATE OR CYANO(CYCLOHEXYLIDENE)ACETATE [J].
GRIFFITHS, G ;
METTLER, H ;
MILLS, LS ;
PREVIDOLI, F .
HELVETICA CHIMICA ACTA, 1991, 74 (02) :309-314
[29]   Triethylborane-mediated atom-transfer cyclisation of 2-iodo-N-(prop-2-enyl)acetamides and related compounds [J].
Ikeda, M ;
Teranishi, H ;
Nozaki, K ;
Ishibashi, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (10) :1691-1697
[30]   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
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