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
Synthesis 2008(13): 2117-2121
DOI: 10.1055/s-2008-1067113
DOI: 10.1055/s-2008-1067113
PAPER
© Georg Thieme Verlag Stuttgart · New YorkHigh-Yield Synthesis of Substituted and Unsubstituted Pyridinium Salts Containing a 4-Oxothiazolidine Moiety
Further Information
Received
12 February 2008
Publication Date:
21 May 2008 (online)
Publication History
Publication Date:
21 May 2008 (online)

Abstract
A new series of unsubstituted and substituted pyridinium salts bearing a 4-oxothiazolidinyl moiety has been prepared by an efficient rearrangement of 2-(1-bromoalkylidene)thiazolidin-4-ones. The process is based on three steps, namely carbon-bromine cleavage, bromine transfer, and substitution, each induced by pyridine or its derivatives, acting as base and reactant.
Key words
pyridinium salts - 4-oxothiazolidine - rearrangement - carbon-bromine cleavage - bromine transfer - nucleophilic substitution
- 1
Zincke T. Justus Liebigs Ann. Chem. 1903, 330: 361 - On biologically active pyridinium salts, see:
- 2a
Yiu S.-H.Knaus EE. J. Med. Chem. 1996, 39: 4576 - 2b
Zheng G.Zhang Z.Pivavarchyk M.Deaciuc AG.Dwoskin LP.Crooks PA. Bioorg. Med. Chem. Lett. 2007, 17: 6734 - 2c
Scott RH.Whyment AD.Foster A.Gordon KH.Milne BF.Jaspars M. J. Membrane Biol. 2000, 176: 119 - 2d
Rao CS.Venkateswarly V.Achaiah G. Bioorg. Med. Chem. Lett. 2006, 16: 2134 - 2e
Michelliza S.Al-Mourabit A.Gateau-Olesker A.Marazano C. J. Org. Chem. 2002, 67: 6474 - For a few examples regarding reactivity of pyridinium salts, see:
- 3a
Nguyen TM.Sanchez-Salvatori M.Wypych J.-C.Marazano C. J. Org. Chem. 2007, 72: 5916 - 3b
Corey EJ.Tian Y. Org. Lett. 2006, 8: 5789 - 3c
Kearney AM.Vanderwal CD. Angew. Chem. Int. Ed. 2006, 45: 7803 - 3d
Kiselyov AS. Tetrahedron Lett. 2005, 46: 4487 - 3e
Alcarazo M.Roseblade SJ.Cowley AR.Fernández R.Brown JM.Lassaletta JM. J. Am. Chem. Soc. 2005, 127: 3290 - 3f
Babaev EV.Efimov AV.Maiboroda DA.Jug K. Eur. J. Org. Chem. 1998, 193 - On selected pyridinium salts, see:
- 4a
Katritzky AR. Tetrahedron 1980, 36: 679 - 4b
Ohno A.Oda S.Yamazaki N. Tetrahedron Lett. 2001, 42: 399 - 4c
Schmidt A. Curr. Org. Chem. 2004, 8: 653 ; and references cited therein - 5a
Viana GHR.Santos IC.Alves RB.Gil L.Marazano C.Gil RPF. Tetrahedron Lett. 2005, 46: 7773 - 5b
Yamaguchi I.Higashi H.Shigesue S.Shingai S.Sato M. Tetrahedron Lett. 2007, 48: 7778 - 6a
Menschutkin J. J. Russ. Phys. Chem. Soc. 1902, 34: 411 - 6b
Yoh S.-D.Cheong D.-Y.Lee O.-S. J. Phys. Org. Chem. 2003, 16: 63 - 7a
Focken T.Charette A. Org. Lett. 2006, 8: 2985 - 7b
Zhang S.-L.Huang Z.-S.An L.-K.Bu X.-Z.Ma L.Li Y.-M.Chan ASC.Gu L.-Q. Org. Lett. 2004, 6: 4853 - 7c
Legault C.Charette AB. J. Am. Chem. Soc. 2003, 125: 6360 - 7d
Palkó R.Riedl Z.Egyed .Fábian L.Hajós G. J. Org. Chem. 2006, 71: 7805 - 7e
Jung ME.Buszek KR. J. Am. Chem. Soc. 1988, 110: 3965 - 7f
Buszek KR.Brown N. Org. Lett. 2007, 9: 707 - 8
Singh SP.Parmar SS.Raman K.Stenberg VI. Chem. Rev. 1981, 81: 175 - 9a
Marković R.Baranac M.D˛ambaski Z. Heterocycles 2004, 63: 851 - 9b
Marković R.D˛ambaski Z.Baranac M. Tetrahedron 2001, 57: 5833 - 9c
Marković R.Baranac M.Juranić N.Macura S.Cekić I.Minić D. J. Mol. Struct. 2006, 800: 85 - 10
Baranac-Stojanović M.Marković R. Tetrahedron Lett. 2007, 48: 1695 - 11 Preliminary communication:
Marković R.Pavlovich JG.Baranac M. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180: 1411 - 12
Zefirov NS.Makhon’kov DI. Chem. Rev. 1982, 82: 615