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 2011(11): 1777-1782
DOI: 10.1055/s-0030-1260025
DOI: 10.1055/s-0030-1260025
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Facile Atom-Economic Synthesis of Imidazoles with Chalcogenophosphoryl Substituents via Free-Radical Addition of Secondary Phosphine Chalcogenides to 1-Vinylimidazoles
Weitere Informationen
Received
13 February 2011
Publikationsdatum:
05. Mai 2011 (online)
Publikationsverlauf
Publikationsdatum:
05. Mai 2011 (online)

Abstract
Secondary phosphine sulfides and selenides react with 1-vinylimidazoles under radical initiation conditions to give the corresponding anti-Markovnikov adducts in up to 98% yields.
Key words
1-vinylimidazoles - phosphine sulfides - phosphine selenides - radical addition
- 1a
Grimmett MR. In Comprehensive Heterocyclic Chemistry II Vol. 3:Katritzky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. p.77-220 - 1b
Hoffmann H.Lindel T. Synthesis 2003, 1753 - 1c
De Luca L. Curr. Med. Chem. 2006, 13: 1 - 1d
Jin Z. Nat. Prod. Rep. 2006, 23: 464 - 1e
Sivappa R.Hernandez NM.He Y.Lovely CJ. Org. Lett. 2007, 9: 3861 - 1f
Bellina F.Cauteruccio S.Rossi R. Tetrahedron 2007, 63: 4571 - 2a
Welton T. Chem. Rev. 1999, 99: 2071 - 2b
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 - 2c
Forsyth SA.Pringle JM.MacFarlane DR. Aust. J. Chem. 2004, 57: 113 - 2d
Chiappe C.Pieraccini D. J. Phys. Org. Chem. 2005, 18: 275 - 2e
Rahman T.Fukuyama T.Ryu I.Suzuki K.Yonemura K.Hughes PF.Nokihara K. Tetrahedron Lett. 2006, 47: 2703 - 2f
Xu J.-M.Liu B.-K.Wu W.-B.Qian C.Wu Q.Lin X.-F. J. Org. Chem. 2006, 71: 3991 - 2g
Greaves TL.Drummond CJ. Chem. Rev. 2008, 108: 206 - 2h
Plaquevent J.-C.Levillain J.Guillen F.Malhiac C.Gaumont A.-C. Chem. Rev. 2008, 108: 5035 - 3a
Ding H.Ma C.Yang Y.Wang Y. Org. Lett. 2005, 7: 2125 - 3b
Pathan MY.Paike VV.Pachmase PR.More SP.Ardhapure SS.Pawar RP. ARKIVOC 2006, (xv): 205 - 4a
Jalil MA.Yamada T.Fujinami S.Hojo T.Nishikawa H. Polyhedron 2001, 20: 627 - 4b
Grotjahn DB.Incarvito CD.Rheingold AL. Angew. Chem. Int. Ed. 2001, 40: 3884 - 4c
Harkal S.Rataboul F.Zapf A.Fuhrmann C.Riermeier T.Monsees A.Beller M. Adv. Synth. Catal. 2004, 346: 1742 - 4d
Grotjahn DB.Gong Y.Zakharov L.Golen JA.Rheingold AL. J. Am. Chem. Soc. 2006, 128: 438 - 4e
Debono N.Canac Y.Duhayon C.Chauvin R. Eur. J. Inorg. Chem. 2008, 2991 - 4f
Canac Y.Debono N.Vendier L.Chauvin R. Inorg. Chem. 2009, 48: 5562 - 4g
Schulz T.Torborg C.Schäffner B.Huang J.Zapf A.Kadyrov R.Börner A.Beller M. Angew. Chem. Int. Ed. 2009, 48: 918 ; Angew. Chem. 2009, 121, 936 - 4h
Field LD.Messerle BA.Vuong KQ.Turner P. Dalton Trans. 2009, 3599 - 5
Trofimov BA.Malysheva SF.Parshina LN.Gusarova NK.Belogorlova NA. Synlett 2011, 94 - 6a
Gusarova NK.Bogdanova MV.Ivanova NI.Chernysheva NA.Sukhov BG.Sinegovskaya LM.Kazheva ON.Alexandrov GG.D’yachenko OA.Trofimov BA. Synthesis 2005, 3103 - 6b
Sukhov BG.Gusarova NK.Ivanova NI.Bogdanova MV.Kazheva ON.Alexandrov GG.D’yachenko OA.Sinegovskaya LM.Malysheva SF.Trofimov BA.
J. Struct. Chem. 2005, 46: 1066 - 6c
Gusarova NK.Malysheva SF.Kuimov VA.Belogorlova NA.Mikhailenko VL.Trofimov BA. Mendeleev Commun. 2008, 18: 260 - 6d
Trofimov BA.Gusarova NK. Mendeleev Commun. 2009, 19: 295 - 6e
Malysheva SF.Artem’ev AV.Gusarova NK.Timokhin BV.Tatarinova AA.Trofimov BA. Russ. J. Gen. Chem. 2009, 79: 1617 - 6f
Gusarova NK.Malysheva SF.Belogorlova NA.Kazheva ON.Chekhlov AN.Alexandrov GG.D’yachenko OA.Sinegovskaya LM.Trofimov BA. J. Struct. Chem. 2010, 51: 120 - 7a
Leca D.Fensterbank L.Lacôte E.Malakria M. Chem. Soc. Rev. 2005, 34: 858 - 7b
Coudray L.Montchamp J.-L. Eur. J. Org. Chem. 2008, 3601 - 7c
Trofimov BA.Gusarova NK.Chernysheva NA.Yas’ko SV.Kazantseva TI.Ushakov IA. Synthesis 2008, 2743 - 8
Jessop CM.Parsons AF.Routledge A.Irvine DJ. Eur. J. Org. Chem. 2006, 1547 - 9a
Gusarova NK.Malysheva SF.Oparina LA.Belogorlova NA.Tantsyrev AP.Parshina LN.Sukhov BG.Tlegenov RT.Trofimov BA. ARKIVOC 2009, (vii): 260 - 9b
Oparina LA.Malysheva SF.Gusarova NK.Vysotskaya OV.Stepanov AV.Belogorlova NA.Albanov AI.Trofimov BA. Synthesis 2009, 3427 - 10a
Shostakovskii MF.Skvortsova GG.Glazkova NP.Domnina ES. Chem. Heterocycl. Compd. 1969, 1070 - 10b
Mamashvili TN.Keiko NA.Kalikhman ID.Domnina ES.Glazkova NP.Voronkov MG. Russ. Chem. Bull. 1987, 2122