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 2009(18): 3150-3156
DOI: 10.1055/s-0029-1216905
DOI: 10.1055/s-0029-1216905
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Efficient Microwave-Assisted Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions in 5-Nitroimidazole Series
Weitere Informationen
Received
6 May 2009
Publikationsdatum:
14. Juli 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. Juli 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200918/lookinside/thumbnails/10.1055-s-0029-1216905-1.jpg)
Abstract
A new simple, rapid and high yielding synthesis (mean yield = 83%) of various 4-aryl, 4-heteroaryl, and 4-styryl-1,2-dimethyl-5-nitro-1H-imidazoles by palladium-catalyzed Suzuki-Miyaura cross-coupling reactions using microwave irradiation is described.
Key words
cross-coupling - 5-nitroimidazoles - palladium - Suzuki reaction - arylations
-
1a
Jorgensen MA.Manos J.Mendz GL.Hazell SL. J. Antimicrob. Chemother. 1998, 41: 67 -
1b
Upcroft JA.Campbell RW.Benakli K.Upcroft P.Vanelle P. Antimicrob. Agents Chemother. 1999, 43: 73 -
1c
Citron DM.Tyrell KL.Warren YA.Fernandez H.Merriam CV.Goldstein EJC. Anaerobe 2005, 11: 315 -
1d
Leitsch D.Kolarich D.Wilson IBH.Altmann F.Duchêne M. PLoS Biol. 2007, 5: e211 -
1e
Crozet MD.Botta C.Gasquet M.Curti C.Rémusat V.Hutter S.Chapelle O.Azas N.De Méo M.Vanelle P. Eur. J. Med. Chem. 2009, 44: 653 -
1f
Kim P.Zhang L.Manjunatha UH.Singh R.Patel S.Jiricek J.Keller TH.Boshoff HI.Barry CE.Dowd CS. J. Med. Chem. 2009, 52: 1329 - 2
Çelik A.Ares Ateş N. Drug Chem. Toxicol. 2006, 29: 85 - 3
Walsh JS.Wang R.Bagan E.Wang CC.Wislocki P.Miwa GT. J. Med. Chem. 1987, 30: 150 - 4
Cudmore SL.Delgaty SF.Hayward-McClelland SF.Petrin DP.Garber GE. Clin. Microbiol. Rev. 2004, 17: 783 - 5
Schwebke JR.Burgess D. Clin. Microbiol. Rev. 2004, 17: 794 - 6
Crowell AL.Sanders-Lewis KA.Secor WE. Antimicrob. Agents Chemother. 2003, 47: 1407 - 7
Upcroft JA.Dunn LA.Wright JM.Benakli K.Upcroft P.Vanelle P. Antimicrob. Agents Chemother. 2006, 50: 344 -
8a
Miyaura N.Yanagi T.Suzuki A. Synth. Commun. 1981, 11: 513 -
8b
Suzuki A. Pure Appl. Chem. 1994, 66: 213 -
8c
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
8d
Handbook
of Palladium Catalysed Organic Reactions
Malleron J.-L.Fiaud J.-C.Legros J.-Y. Academic Press; San Diego: 1997. -
8e
Suzuki A. In Metal-Catalysed Cross-Coupling ReactionsDiederich F.Stang PJ. VCH; Weinheim: 1998. p.49-97 -
8f
Stanforth SP. Tetrahedron 1998, 54: 263 -
8g
Suzuki A. J. Organomet. Chem. 1999, 576: 147 -
8h
Genet J.-P.Savignac M. J. Organomet. Chem. 1999, 576: 305 -
8i
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9633 -
8j
Suzuki A. J. Organomet. Chem. 2002, 653: 83 -
8k
Suzuki A.Brown HC. Organic Syntheses via Boranes Vol. 3: Aldrich; Milwaukee: 2003. -
8l
Enguehard-Gueiffier C.Hübner H.El Hakmaoui A.Allouchi H.Gmeiner P.Argiolas A.Melis MR.Gueiffier A. J. Med. Chem. 2006, 49: 3938 -
8m
Véron J.-B.Enguehard-Gueiffier C.Snoeck R.Andrei G.De Clercq E.Gueiffier A. Bioorg. Med. Chem. 2007, 15: 7209 -
9a
Kawasaki I.Yamashita M.Ohta S. Chem. Pharm. Bull. 1996, 44: 1831 -
9b
Kawasaki I.Katsuma H.Nakayama Y.Yamashita M.Ohta S. Heterocycles 1998, 48: 1887 -
9c
Langhammer I.Erker T. Heterocycles 2005, 65: 1975 -
9d
Zhang P.Zhang N.Buckwold VE.Hosmane RS. Bioorg. Med. Chem. 2007, 15: 4933 -
9e
Zhang P.Zhang N.Korba BE.Hosmane RS. Bioorg. Med. Chem. Lett. 2007, 17: 2225 -
9f
Angell RM.Angell TD.Bamborough P.Brown D.Brown M.Buckton JB.Cockerill SG.Edwards CD.Jones KL.Longstaff T.Smee PA.Smith KJ.Somers DO.Walker AL.Willson M. Bioorg. Med. Chem. Lett. 2008, 18: 324 - 10
Bellina F.Cauteruccio S.Rossi R. J. Org. Chem. 2007, 72: 8543 -
11a
Shapiro G.Gomez-Lor B. J. Org. Chem. 1994, 59: 5524 -
11b
Revesz L.Di Padova FE.Buhl T.Feifel R.Gram H.Hiestand P.Manning U.Wolf R.Zimmerlin AG. Bioorg. Med. Chem. Lett. 2002, 12: 2109 -
11c
Nonell S.Borrell JI.Borrós S.Colominas C.Rey O.Rubio N.Sánchez-García D.Teixidó J. Eur. J. Med. Chem. 2003, 1635 -
11d
Chittiboyina AG.Raji Reddy Ch.Watkins EB.Avery MA. Tetrahedron Lett. 2004, 45: 1869 -
11e
Roppe J.Smith ND.Huang D.Tehrani L.Wang B.Anderson J.Brodkin J.Chung J.Jiang X.King C.Munoz B.Varney MA.Prasit P.Cosford DP. J. Med. Chem. 2004, 47: 4645 -
11f
Cerezo V.Afonso A.Planas M.Feliu L. Tetrahedron 2007, 63: 10445 - 12
Crozet MD.Castera-Ducros C.Vanelle P. Tetrahedron Lett. 2006, 47: 7061 - 13
Sunjic V.Fajdiga T.Japelj M.Rems P. J. Heterocycl. Chem. 1969, 6: 53 - 14
Bhujanga Rao AKS.Gundu Rao C.Singh BB. J. Org. Chem. 1992, 57: 3240 - 15
Fitzmaurice C, andLord GH. inventors; British Patent GB 19620802. ; Chem. Abstr. 1966, 66, 37927 - 16
Erker T.Handler N. Sci. Pharm. 2004, 72: 15 - 17
Ross WJ.Todd A. J. Med. Chem. 1973, 16: 863
References
Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2, 1EZ, UK; fax: +44 (1223)336033; email: deposit@ccdc.cam.ac.uk. (compound 20: CCDC # 704224 and compound 21: CCDC # 716232). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.