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Synthesis 2007(8): 1242-1246
DOI: 10.1055/s-2007-965980
DOI: 10.1055/s-2007-965980
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Pyrroles via Copper-Catalyzed Coupling of Amines with Bromoenones
Weitere Informationen
Received
7 February 2007
Publikationsdatum:
12. März 2007 (online)
Publikationsverlauf
Publikationsdatum:
12. März 2007 (online)
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Abstract
The CuI/N,N-dimethylglycine hydrochloride catalyzed reactions of amines with γ-bromo-substituted γ,δ-unsaturated ketones in the presence of K3PO4 and NH4OAc led to the formation of the corresponding polysubstituted pyrroles in good to excellent yields.
Key words
Ullmann-type reaction - amine - pyrrole - ammonium acetate
- For reviews, see:
-
1a
Comprehensive Heterocyclic Chemistry
Vol. 2:
Katritzky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. -
1b
Joule JA.Mills K. In Heterocyclic Chemistry Blackwell Science; Oxford: 2000. Chap. 13. -
1c
Balme G. Angew. Chem. Int. Ed. 2004, 43: 6238 - 2 For a review, see:
Electronic Materials: The Oligomer Approach
Müllen K.Wegner G. Wiley-VCH; Weinheim: 1998. - 3 For a review article, see:
Sundberg RJ. In Comprehensive Heterocyclic Chemistry Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. p.119 - For recent selected examples, see:
-
4a
Hiroya K.Matsumoto S.Ashikawa M.Ogiwara K.Sakamoto T. Org. Lett. 2006, 8: 5349 -
4b
Wimkler JD.Ragains JR. Org. Lett. 2006, 8: 4031 -
4c
Ishikawa T.Aikawa T.Watanabe S.Saito S. Org. Lett. 2006, 8: 3881 -
4d
Shimizu M.Takahashi A.Kawai S. Org. Lett. 2006, 8: 3585 -
4e
Lu L.Chen G.Ma S. Org. Lett. 2006, 8: 835 -
4f
Wang C.Wang Z.Liu L.Wang C.Liu G.Xi Z. J. Org. Chem. 2006, 71: 8565 -
4g
Dong C.Deng G.Wang J. J. Org. Chem. 2006, 71: 5560 -
4h
Freifeld I.Shojaei H.Langer P. J. Org. Chem. 2006, 71: 4965 -
4i
Harrison TJ.Kozak JA.Corbella-Pane M.Dake GR. J. Org. Chem. 2006, 71: 4525 -
4j
Moonen K.Dieltiens N.Stevens CV. J. Org. Chem. 2006, 71: 4006 -
4k
Wang X.Xing D.Fang Z.Li B.Zhao F.Zhang K.Yang L.Shi Z. J. Am. Chem. Soc. 2006, 128: 12046 -
4l
Bianchi I.Forlani R.Minetto G.Peretto I.Regalia N.Taddei M.Raveglia LF. J. Comb. Chem. 2006, 8: 491 - For reviews, see:
-
5a
Kunz K.Scholz U.Ganzer D. Synlett 2003, 2428 -
5b
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
5c
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 -
5d
Deng W.Liu L.Guo QX. Chin. J. Org. Chem. 2004, 24: 150 ; Chem. Abstr. 2004, 140, 406327 -
5e
Dehli JR.Legros J.Bolm C. Chem. Commun. 2005, 973 -
5f
Corbet J.-P.Mignani G. Chem. Rev. 2006, 106: 2651 - For the latest examples, see:
-
6a
Wang Z.Bao W.Jiang Y. Chem. Commun. 2005, 2849 -
6b
Trost BM.Stiles DT. Org. Lett. 2005, 7: 2117 -
6c
Shen L.Hsung RP.Zhang Y.Antoline JE.Zhang X. Org. Lett. 2005, 7: 3081 -
6d
Ma D.Cai Q.Xie X. Synlett 2005, 1767 -
6e
Dehli JR.Bolm C. Adv. Synth. Catal. 2005, 347: 239 -
6f
Ouali A.Laurent R.Caminade A.-M.Majoral J.-P.Taillefer M. J. Am. Chem. Soc. 2006, 128: 15990 -
6g
Yuen J.Fang Y.-Q.Lautens M. Org. Lett. 2006, 8: 653 -
6h
Miyamoto H.Okawa Y.Nakazaki A.Kobayashi S. Angew. Chem. Int. Ed. 2006, 45: 2274 -
6i
Zheng Y.Du X.Bao W. Tetrahedron Lett. 2006, 47: 1217 -
6j
Taillefer M.Ouali A.Renard B.Spindler J. Chem. Eur. J. 2006, 12: 5301 -
6k
Chang D.Bao W. Synlett 2006, 1786 -
6l
Pei L.Qian W. Synlett 2006, 1719 -
6m
Martin R.Rivero MR.Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 7079 -
6n
Toumi M.Couty F.Evano G. Angew. Chem. Int. Ed. 2007, 46: 572 -
6o
Wang Z.Mo H.Bao W. Synlett 2007, 91 -
7a
Lu H.Li C. Org. Lett. 2006, 8: 5365 -
7b
Fang Y.Li C. J. Org. Chem. 2006, 71: 6427 -
7c
Fang Y.Li C. Chem. Commun. 2005, 3574 -
7d
Hu T.Li C. Org. Lett. 2005, 7: 2035 - 8
Tanyeli C.Akhmedov IM.Yazicioglu EY. Tetrahedron Lett. 2004, 45: 9627 -
9a
Mori M.Washioka Y.Urayama T.Yoshiura K.Chiba K.Ban Y. J. Org. Chem. 1983, 48: 4058 -
9b
Trost BM.Chen DWC. J. Am. Chem. Soc. 1996, 118: 12541 - 10
Arcadi A.Rossi E. Tetrahedron 1998, 54: 15253 - 11
Ahlbrecht H.Von Daacke A. Synthesis 1984, 610 - 12
Trofimov BA.Tarasova OA.Mikhaleva AI.Kalinina NA.Sinegovskaya LM.Henkelmann J. Synthesis 2000, 1585 - 13
Yagi T.Aoyama T.Shioiri T. Synlett 1997, 1063 - 14
Curini M.Montanari F.Rosati O.Lioy E.Margarita R. Tetrahedron Lett. 2003, 44: 3923