2,4-vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts

被引：113
作者：
Chen, Feng [1 ]
Shen, Tao [1 ]
Cui, Yuxin [1 ]
Jiao, Ning [1 ,2 ]
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 18期
基金：
美国国家科学基金会;
关键词：
VINYL AZIDES; C-H; POLYSUBSTITUTED PYRROLES; SUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; DERIVATIVES; CYCLIZATION; CHEMISTRY; ROUTE; 2,4-DIARYLPYRROLES;
D O I：
10.1021/ol302270z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.
引用
收藏
页码：4926 / 4929
页数：4
相关论文
共 73 条
[1]   One-pot synthesis of 4,5-dihydro-1H-pyrrol-3-carboxamide derivatives via a four-component reaction [J].
Alizadeh, Abdolah ;
Rezvanian, Atieh ;
Zhu, Long-Guan .
TETRAHEDRON, 2008, 64 (02) :351-355
[2]   PYRROLE CHEMISTRY .28. SUBSTITUTION-REACTIONS OF 1-(PHENYLSULFONYL)PYRROLE AND SOME DERIVATIVES [J].
ANDERSON, HJ ;
LOADER, CE ;
XU, RX ;
LE, N ;
GOGAN, NJ ;
MCDONALD, R ;
EDWARDS, LG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (04) :896-902
[3]   Synthesis and screening for antiacetylcholinesterase activity of (1-benzyl-4-oxopiperidin-3-ylidene)methylindoles and -pyrroles related to donepezil [J].
Andreani, A ;
Cavalli, A ;
Granaiola, M ;
Guardigli, M ;
Leoni, A ;
Locatelli, A ;
Morigi, R ;
Rambaldi, M ;
Recanatini, M ;
Roda, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4011-4014
[4]  
[Anonymous], 1998, Electronic materials: the oligomer approach
[5]  
[Anonymous], 1992, PYRROLES 2
[6]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[7]   Design, synthesis, and biological evaluation of hybrid molecules containing α-methylene-γ-butyrolactones and polypyrrole minor groove binders [J].
Baraldi, PG ;
Nunez, MD ;
Tabrizi, MA ;
De Clercq, E ;
Balzarini, J ;
Bermejo, J ;
Estévez, F ;
Romagnoli, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (11) :2877-2886
[8]   Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles [J].
Bergner, Ines ;
Wiebe, Christine ;
Meyer, Nino ;
Opatz, Till .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8243-8253
[9]   Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].
Binder, JT ;
Kirsch, SF .
ORGANIC LETTERS, 2006, 8 (10) :2151-2153
[10]   Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination [J].
Bonnamour, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2011, 13 (08) :2012-2014
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