2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

被引:23
作者
Clark, Andrew J. [1 ]
Coles, Stuart R. [1 ]
Collis, Alana [1 ]
Fullaway, David R. [1 ]
Murphy, Nicholas P. [1 ]
Wilson, Paul [1 ]
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
基金
英国工程与自然科学研究理事会;
关键词
Copper; ATRC; Atom transfer; Radical; Aryl migration; Dimethylpiperazine; COPPER-CATALYZED CYCLIZATION; N-ALLYLTRICHLOROACETAMIDES; GAMMA-LACTAMS; BIARYLS;
D O I
10.1016/j.tetlet.2009.08.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6311 / 6314
页数:4
相关论文
共 32 条
[1]   The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].
Beesley, RM ;
Ingold, CK ;
Thorpe, JF .
JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106
[2]  
Bonfand E, 2000, SYNLETT, P475
[3]  
Bossart M, 2002, EUR J ORG CHEM, V2002, P2742
[4]   Metal-catalysed radical cyclisations leading to N-heterocycles:: new approaches to gabapentin and pulchellalactam [J].
Bryans, JS ;
Chessum, NEA ;
Huther, N ;
Parsons, AF ;
Ghelfi, F .
TETRAHEDRON, 2003, 59 (33) :6221-6231
[5]   Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni:: an effective approach to gabapentin [J].
Cagnoli, R ;
Ghelfi, F ;
Pagnoni, UM ;
Parsons, AF ;
Schenetti, L .
TETRAHEDRON, 2003, 59 (50) :9951-9960
[6]   Solid-supported copper catalysts for atom-transfer radical cyclizations: Assessment of support type and ligand structure on catalyst performance in the synthesis of nitrogen heterocycles [J].
Clark, AJ ;
Geden, JV ;
Thom, S .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1471-1479
[7]   Atom transfer radical cyclisation reactions mediated by copper complexes [J].
Clark, AJ .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :1-11
[8]   Ligand geometry effects in copper mediated atom transfer radical cyclisations. [J].
Clark, AJ ;
Filik, RP ;
Thomas, GH .
TETRAHEDRON LETTERS, 1999, 40 (26) :4885-4888
[9]   Ligand electronic effects on rates of copper mediated atom transfer radical cyclisation and polymerisation [J].
Clark, AJ ;
Battle, GM ;
Heming, AM ;
Haddleton, DM ;
Bridge, A .
TETRAHEDRON LETTERS, 2001, 42 (10) :2003-2005
[10]   5-exo atom transfer cyclisation onto alkynes mediated by copper(I) complexes [J].
Clark, AJ ;
Battle, GM ;
Bridge, A .
TETRAHEDRON LETTERS, 2001, 42 (10) :1999-2001