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-00000083.xml
Synlett 2007(2): 0211-0214
DOI: 10.1055/s-2007-967998
DOI: 10.1055/s-2007-967998
LETTER
© Georg Thieme Verlag Stuttgart · New York
Practical Regioselective Bromination of Azaindoles and Diazaindoles
Weitere Informationen
Received
31 October 2006
Publikationsdatum:
24. Januar 2007 (online)
Publikationsverlauf
Publikationsdatum:
24. Januar 2007 (online)
Abstract
A mild and efficient synthesis of various 3-brominated azaindoles and diazaindoles was developed by regioselective halogenation of the parent systems. This practical and high-yielding transformation was achieved with copper(II) bromide in acetonitrile at room temperature.
Key words
3-brominated azaindoles - regioselective halogenation - copper(II) bromide
- 2
Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000, 1045 ; and references therein -
3a
Messaoudi S.Anizon F.Pfeiffer B.Golsteyn R.Prudhomme M. Tetrahedron Lett. 2004, 45: 4643 -
3b
Wang T.Zhang Z.Wallace OB.Deshpande M.Fang H.Yang Z.Zadjura LM.Tweedie DL.Haung S.Zhao F.Ranadive S.Robinson BS.Gong Y.-F.Ricarrdi K.Spicer TP.Deminie C.Rose R.Wang H.-GH.Blair WS.Shi P.-Y. J. Med. Chem. 2003, 46: 4236 -
3c
Marminon C.Pierré A.Pfeiffer B.Pérez V.Léonce S.Prudhomme M. J. Med. Chem. 2003, 46: 609 -
3d
Ujjainwalla F.Walsh TF. Tetrahedron Lett. 2001, 42: 6441 -
3e
Cooper LC.Chicchi GG.Dinnell K.Elliott JM.Hollingworth GJ.Kurtz MM.Locker KL.Morrison D.Shaw DE.Tsao K.-L.Watt AP.Williams AR.Swain CJ. Bioorg. Med. Chem. Lett. 2001, 11: 1233 -
3f
Minakata S.Hamada T.Komatsu M.Tsuboi H.Kikuta H.Ohshiro Y. J. Agric. Food Chem. 1997, 45: 2345 -
3g
Kunick C.Lauenroth K.Leost M.Meijer L.Lemcke T. Bioorg. Med. Chem. Lett. 2004, 14: 413 -
3h
Trejo A.Arzeno H.Browner M.Chanda S.Cheng S.Comer DD.Dalrymple SA.Dunten P.Lafargue J.Lovejoy B.Freire-Moar J.Lim J.Mcintosh J.Miller J.Papp E.Reuter D.Roberts R.Sanpablo F.Saunders J.Song K.Villasenor A.Warren SD.Welch M.Weller P.Whiteley PE.Zeng L.Goldstein DM. J. Med. Chem. 2003, 46: 4702 -
3i
Fisher M.Schwartzkopf G.Hoff DR. J. Med. Chem. 1972, 15: 1168 -
4a
Mettey Y.Gompel M.Thomas V.Garnier M.Leost M.Ceballos-Picot I.Noble M.Endicott J.Vierfond J.-M.Meijer L. J. Med. Chem. 2003, 46: 222 -
4b
Meade EA.Wotring LL.Drach JC.Townsend LB. J. Med. Chem. 1997, 40: 794 -
5a
Harcken C.Ward Y.Thomson D.Riether D. Synlett 2005, 3121 -
5b
Kuzmich D.Mulrooney C. Synthesis 2003, 1671 -
5c
Lachance N.April M.Joly M.-A. Synthesis 2005, 2571 -
5d
Roy PJ.Dufresne C.Lachance N.Leclerc J.-P.Boisvert M.Wang Z.Leblanc Y. Synthesis 2005, 2751 -
5e
Lefoix M.Daillant J.-P.Routier S.Mérour J.-Y.Cillaizeau I.Coudert G. Synthesis 2005, 3581 -
5f
Schirok H. Synlett 2005, 1255 -
5g
Lomberget T.Radix S.Barret R. Synlett 2005, 2080 -
5h
Beccalli EM.Broggini G.Martinelli M.Paladino G. Tetrahedron 2005, 61: 1077 -
5i
Koradin C.Dohle W.Rodriguez AL.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 -
5j
Hopkins CR.Collar N. Tetrahedron Lett. 2005, 46: 1845 -
5k
Cottineau B.O’Shea DF. Tetrahedron Lett. 2005, 46: 1935 -
5l
Debenham SD.Chan A.Liu K.Price K.Wood HB. Tetrahedron Lett. 2005, 46: 2283 -
6a
Prokopov AA.Yakhontov LN. Khim. Geterotsikl. Soedin. 1978, 496 -
6b
Yakhontov LN.Azimov VA.Lapan EI. Tetrahedron Lett. 1969, 10: 1909 -
6c
Alvarez M.Fernandez D.Joule JA. Synthesis 1999, 615 -
6d
Minakata S.Komatsu M.Ohshiro Y. Synthesis 1992, 661 -
6e
Zhang Z.Yang Z.Wong H.Zhu J.Meanwell NA.Kadow JF.Wang T. J. Org. Chem. 2002, 67: 6226 - 7
Gallou F.Reeves JT.Tan Z.Song JJ.Yee NK.Campbell S.Jones P.-J.Senanayake CH. Synlett 2005, 2400 - 8
Sloan MJ.Phillips RS. Bioorg. Med. Chem. Lett. 1992, 2: 1053 - 9
Hands D.Bishop B.Cameron M.Edwards JS.Cottrell IF.Wright SHB. Synthesis 1996, 877 - 10
Kelly TA.McNeil DW.Rose JM.David E.Shih C.-K.Grob PM. J. Med. Chem. 1997, 40: 2430 - 11
Alvarez M.Fernández D.Joule JA. Synthesis 1999, 615
References and Notes
Current address: Novartis Pharma AG, Chemical and Analytical Development, Werk Klybeck, Postfach, 4002 Basel, Switzerland. This address should be used for correspondence.