RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(10): 1625-1628
DOI: 10.1055/s-0029-1218703
DOI: 10.1055/s-0029-1218703
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient New Method for the Synthesis of Polysubstituted Pyrroles [¹]
Weitere Informationen
Received
1 February 2010
Publikationsdatum:
15. März 2010 (online)
Publikationsverlauf
Publikationsdatum:
15. März 2010 (online)
Abstract
The three-component reactions of phenacyl bromide or its derivatives, amine, and dialkyl acetylenedicarboxylate in the presence of iron(III) chloride as a catalyst at room temperature afforded polysubstituted pyrroles in high yields.
Key words
polysubstituted pyrroles - three-component reaction - iron(III) chloride
Part 283 in the series ‘Studies on Novel Synthetic Methodologies’.
-
2a
Finar IL. Organic Chemistry: Stereochemistry and Chemistry of Natural Products 5th ed., Vol. 2: Longman; London: 1975. p.885-913 -
2b
O’Hagan D. Nat. Prod. Rep. 2000, 17: 435 -
2c
Walsh CT.Garneau-Tsodikova S.Howard-Jones AR. Nat. Prod. Rep. 2006, 23: 517 -
3a
Huffman JW. Curr. Med. Chem. 1999, 6: 705 -
3b
Kidwai M.Venkataramanan R.Mohan R.Sapra P. Curr. Med. Chem. 2002, 9: 1209 -
3c
La Regina G.Silvestri R.Artico M.Lavechia A.Novellino E.Befani O.Turini P.Agostinelli E. J. Med. Chem. 2007, 50: 922 -
4a
Boger DL.Boyce CW.Labrilli MA.Sehon CA.Jin Q. J. Am. Chem. Soc. 1999, 121: 54 -
4b
Abid M.Landge SM.Torok B. Org. Prep. Proced. Int. 2006, 38: 495 -
5a
Facchetti A.Abboto A.Beverina L.van der Boom ME.Dutta P.Evmenenko G.Pagani GA.Marks TJ. Chem. Mater. 2003, 15: 1064 -
5b
Pu S.Liu G.Shen L.Xu J. Org. Lett. 2007, 9: 2139 - Some recent examples:
-
6a
Larionov OV.de Meijere A. Angew. Chem. Int. Ed. 2005, 44: 5664 -
6b
Minetto G.Raveglia LF.Sega A.Taddei M. Eur. J. Org. Chem. 2005, 24: 5277 -
6c
Shiner CM.Laner TD. Tetrahedron 2005, 61: 11628 -
6d
Hwang SJ.Cho SH.Chang S.
J. Am. Chem. Soc. 2008, 130: 16158 -
6e
Abid M.Teixeira L.Torok B. Org. Lett. 2008, 10: 933 -
6f
La YD.Arndtsen BA. Angew. Chem. Int. Ed. 2008, 47: 5430 -
7a
Das B.Balasubramanyam P.Krishnaiah M.Veeranjaneyulu B.Reddy GC. J. Org. Chem. 2009, 74: 4393 -
7b
Das B.Damodar K.Bhunia N. J. Org. Chem. 2009, 74: 5607 -
7c
Das B.Satyalakshmi G.Suneel K.Damodar K. J. Org. Chem. 2009, 74: 8400 -
7d
Das B.Balasubramanyam P.Veeranjaneyulu B.Reddy GC.
J. Org. Chem. 2009, 74: 9505 - 8
Zhu Q.Jiang H.Li J.Zhang M.Wang X.Qi C. Tetrahedron 2009, 65: 4604
References
Part 283 in the series ‘Studies on Novel Synthetic Methodologies’.