Gold(I)-Catalyzed Rearrangement of N-Aryl 2-Alkynylazetidines to Pyrrolo[1,2-a]indoles

被引:37
作者
Kern, Nicolas [1 ]
Hoffmann, Marie [1 ]
Blanc, Aurelien [1 ]
Weibel, Jean-Marc [1 ]
Pale, Patrick [1 ]
机构
[1] Univ Strasbourg, Inst Chim, CNRS, Lab Synth Reactivite Organ & Catalyse, F-67070 Strasbourg, France
关键词
CLAISEN REARRANGEMENT; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; GOLD CATALYSIS; ANTIBIOTICS;
D O I
10.1021/ol303518n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various N-aryl-2-alkynylazetidines were very efficiently converted to pyrrolo[1,2-a]indoles with gold catalysts, especially the 2-biphenyl-dicyclohexylphosphino-gold(I) hexafluoroantimonate, in dichloromethane at room temperature. Additionally, two formal syntheses of bioactive non-natural compounds, i.e. 7-methoxymitosene and an 5-HT2c receptor agonist, have been achieved.
引用
收藏
页码:836 / 839
页数:4
相关论文
共 42 条
[1]   MITOMYCIN ANTIBIOTICS . SYNTHETIC STUDIES .2. SYNTHESIS OF 7-METHOXYMITOSENE ANTIBACTERIAL AGENT [J].
ALLEN, GR ;
POLETTO, JF ;
WEISS, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3877-&
[2]   Mitomycins syntheses: a recent update [J].
Andrez, Jean-Christophe .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5
[3]   Silver and Gold Catalysis for Cycloisomerization Reactions [J].
Belmont, Philippe ;
Parker, Evelyne .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) :6075-6089
[4]   Mitomycin C: a clinical update [J].
Bradner, WT .
CANCER TREATMENT REVIEWS, 2001, 27 (01) :35-50
[5]  
Britton J, 2012, CHIM OGGI, V30, P6
[6]   Thermally induced [3+2] cyclization of aniline-tethered alkylidenecyclopropanes: a facile synthetic protocol of pyrrolo[1,2-a]indoles [J].
Chen, Kai ;
Zhang, Zhen ;
Wei, Yin ;
Shi, Min .
CHEMICAL COMMUNICATIONS, 2012, 48 (62) :7696-7698
[7]   Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].
Corma, A. ;
Leyva-Perez, A. ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712
[8]  
Gagosz F, 2010, ACTUAL CHIMIQUE, P12
[9]   Gold catalysis [J].
Hashmi, A. Stephen K. ;
Hutchings, Graham J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :7896-7936
[10]   Gold Catalysis: 1,3-Oxazines by Cyclisation of Allene Amides [J].
Hashmi, A. Stephen K. ;
Schuster, Andreas M. ;
Litters, Sebastian ;
Rominger, Frank ;
Pernpointner, Markus .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (20) :5661-5667