Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2006(22): 3855-3858
DOI: 10.1055/s-2006-950303
DOI: 10.1055/s-2006-950303
PAPER
© Georg Thieme Verlag Stuttgart · New YorkOne-Step Polyfunctionalization of (Methylthio)thiophenes
Further Information
Received
6 July 2006
Publication Date:
09 October 2006 (online)
Publication History
Publication Date:
09 October 2006 (online)
Abstract
The one-step polyfunctionalization of 2- and 3-(methylthio)thiophenes was investigated. Direct polymetalation with superbases followed by quenching with an appropriate electrophile led to 2,αS-disubstituted derivatives starting from 2-(methylthio)thiophene, and 2,5,αS-trisubstituted derivatives starting from 3-(methylthio)thiophene.
Key words
heterocycles - metalation - regioselectivity - superbases - thiophenes
- 1
Hrib NJ.Jurcak JG.Bregna DE.Dunn RW.Geyer HM.Hartman HB.Roehr JE.Rogers KL.Rush DK.Szczepanik AM.Szewerak MR.Wilmot CA.Conway PG. J. Med. Chem. 1992, 35: 2712 ; and references cited therein - 2
Connor DT.Cetenko WA.Mullican MD.Sorenson RJ.Unangst P.Weikert RJ.Adolphson RL.Kennedy JA.Thueson DO.Wright C.Conroy MC. J. Med. Chem. 1992, 35: 958 ; and references cited therein - 3
Ahlheim M.Barzoukas M.Bedworth PV.Blanchard-Desce M.Fort A.Hu ZY.Marder SR.Perry JW.Runser C.Staehelin M.Zysset B. Science (Washington DC) 1996, 271: 335 - 4
Benincori T.Gladiali S.Rizzo S.Sannicolò F. J. Org. Chem. 2001, 66: 5940 - 5
Mandal SS.Samanta SS.Deb C.De A. J. Chem. Soc., Perkin Trans. 1 1998, 2559 - 6
Mukherjee C.Kamila S.De A. Tetrahedron 2003, 59: 4767 - 7
Snieckus V. Chem. Rev. 1990, 90: 879 ; and references cited thereinMissingFormLabel - 8
Cabiddu S.Floris C.Melis S. Tetrahedron Lett. 1986, 27: 4625 - 9
Cabiddu S.Fattuoni C.Floris C.Gelli G.Melis S. J. Organomet. Chem. 1992, 441: 197 - 10
Cabiddu S.Fattuoni C.Floris C.Gelli G.Melis S. Tetrahedron 1993, 49: 4965 - 11
Brandsma L.Verkruijsse H. In Preparative Polar Organometallic Chemistry 1 Springer-Verlag; Berlin: 1987. Chap. V.MissingFormLabel - 12
Schlosser M. In Modern Synthetic Methods Vol. 6:Scheffold R. Verlag HCA; Basel and VCH: Weinheim: 1992.MissingFormLabel - 13
Clayden J. In Organolithium: Selectivity for Synthesis Pergamon; Amsterdam: 2002. p.207MissingFormLabel - 14
Duhamel L.Plaquevent JC. J. Org. Chem. 1979, 44: 3404 - 15
Gol’dfarb YaL.Pokhil GP.Belen’kii LI. J. Gen. Chem. USSR 1967, 37: 2541