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(12): 1960-1962
DOI: 10.1055/s-0029-1216808
DOI: 10.1055/s-0029-1216808
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAn Efficient Synthesis of Tetraalkyl 2,3,4,5-Thiophenetetracarboxylate Derivatives
Weitere Informationen
Received
8 February 2009
Publikationsdatum:
12. Mai 2009 (online)
Publikationsverlauf
Publikationsdatum:
12. Mai 2009 (online)

Abstract
A facile and direct synthetic entry to tetraalkyl 2,3,4,5-thiophenetetracarboxylate derivatives is described. This involves the reaction of dialkyl acetylenedicarboxylates with elemental sulfur in the presence of triethyl phosphite or an N-heteroaromatic compound such as isoquinoline, 1-methyl-1H-imidazole, or pyridine as catalyst.
Key words
dialkyl acetylenedicarboxylate - elemental sulfur - catalytic reaction - tetraalkyl 2,3,4,5-thiophenetetracarboxylate
- 1a
Eicher T.Hauptmann S.Speicher A. The Chemistry of Heterocycles Wiley-VCH; New York: 2003. Chap. 5. p.Section 5.6MissingFormLabel - 1b
Gronowitz S. In The Chemistry of Heterocyclic Compounds: Thiophene and its Derivatives Vol. 44:Gronowitz S. Wiley; New York: 1991.MissingFormLabel - 2
Koike K.Jia Z.Nikaib T.Liu Y.Guo D. Org. Lett. 1999, 1: 197 - 3a
Luker TJ.Beaton HG.Whiting M.Kete A.Cheshire DR. Tetrahedron Lett. 2000, 41: 7731MissingFormLabel - 3b
Holmes JM.Lee GCM.Wijino M.Weinkam R.Wheeler LA.Garst ME. J. Med. Chem. 1994, 37: 1646MissingFormLabel - 4
Roncali J. Chem. Rev. 1997, 97: 173 - 5
Schopf G.Kossemehl G. Adv. Polym. Sci. 1997, 129: 1 - 6
Kiani MS.Mitchell GR. Synth. Met. 1992, 46: 293 - 7
Wolf JJ.Wortmann R. Adv. Phys. Org. Chem. 1999, 32: 121 - 8
Li XC.Sirringhaus H.Garrier F.Holmes AB.Morratti SC.Feeder N.Clegg W.Teat SJ.Friend RH. J. Am. Chem. Soc. 1998, 120: 2206 - 9
Greenham NC.Morratti SC.Bradley DDC.Friend RH.Holmes AB. Nature 1993, 365: 628 - 10
Russell RK.Press JB. In Comprehensive Heterocyclic Chemistry IIKatritzky AR.Rees CW.Scriven EFV. Pergamon; London: 1996.MissingFormLabel - 11a
Shevchenko NE.Nenajdenko VG.Balenkova ES. Synthesis 2003, 1191MissingFormLabel - 11b
Barbarella G.Melucci M.Sotgiu G. Adv. Mater. 2005, 17: 1581MissingFormLabel - 11c
Masui K.Ikegami H.Mori A. J. Am. Chem. Soc. 2004, 126: 5074MissingFormLabel - 12a
Zhang H.Yang G.Chen J.Chen Z. Synthesis 2004, 3055MissingFormLabel - 12b
Koji S.Satoshi K. Synthesis 1982, 1056MissingFormLabel - 12c
Hideo K.Keiichi N.Kazuhiko Y.Hiroo I. Synthesis 1996, 1193MissingFormLabel - 13a
Bartolo G.Giuseppe S.Alessia F. Org. Lett. 2000, 2: 351MissingFormLabel - 13b
Fazio A.Gabriele B.Salerno G.Destri S. Tetrahedron 1999, 55: 485MissingFormLabel - 13c
Ong CW.Chen CM.Wang LF.Shieh PC. Tetrahedron Lett. 1998, 39: 9191MissingFormLabel - 13d
Stephensen H.Zaragona F. J. Org. Chem. 1997, 62: 6096MissingFormLabel - 14
Gewald K. Angew. Chem. 1961, 73: 114 - 15a
Sommen G.Comel A.Kirsch G. Synlett 2001, 1731MissingFormLabel - 15b
Msahraqui SH.Hariharasubrahmanian H.Kumar S. Synthesis 1999, 2030MissingFormLabel - 15c
Sommen G.Comel A.Kirsch G. Tetrahedron Lett. 2002, 43: 257MissingFormLabel - 16
Kirsch G.Prim D. Synth. Commun. 1994, 24: 1721 - 17
Majumdar KC.Das U. J. Org. Chem. 1998, 63: 9997 - 18a
Alizadeh A.Masrouri H.Rostamnia S.Movahedi F. Helv. Chim. Acta 2006, 89: 923MissingFormLabel - 18b
Alizadeh A.Rostamnia S.Hu ML. Synlett 2006, 1592MissingFormLabel - 18c
Alizadeh A.Rostamnia S.Zhu LG. Tetrahedron 2006, 62: 5641MissingFormLabel - 19a
Alizadeh A.Rostamnia S.Zohreh N.Oskueyan Q. Synlett 2007, 1610MissingFormLabel - 19b
Alizadeh A.Rostamnia S.Esmaili AA. Synthesis 2007, 709MissingFormLabel - 19c
Alizadeh A.Oskueyan Q.Rostamnia S. Synthesis 2007, 2637MissingFormLabel - 20a
Alizadeh A.Hosseinpour R.Rostamnia S. Synthesis 2008, 2462MissingFormLabel - 20b
Alizadeh A.Hosseinpour R.Rostamnia S. Synthesis 2008, 3742MissingFormLabel - 21
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathess JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 - 22a
Huisgen R.Herbig K. Liebigs Ann. Chem. 1965, 688: 98MissingFormLabel - 22b
Huisgen R.Morikawa M.Herbig K.Brunn E. Chem. Ber. 1967, 100: 1094MissingFormLabel - 22c
Winterfeldt E. Chem. Ber. 1965, 98: 3537MissingFormLabel - 23a
Zbiral E. Synthesis 1974, 775MissingFormLabel - 23b
Becker KB. Tetrahedron 1987, 36: 1717MissingFormLabel