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Synthesis 2009(12): 1960-1962
DOI: 10.1055/s-0029-1216808
DOI: 10.1055/s-0029-1216808
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Synthesis of Tetraalkyl 2,3,4,5-Thiophenetetracarboxylate Derivatives
Further Information
Received
8 February 2009
Publication Date:
12 May 2009 (online)
Publication History
Publication Date:
12 May 2009 (online)
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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 5.6 -
1b
Gronowitz S. In The Chemistry of Heterocyclic Compounds: Thiophene and its Derivatives Vol. 44:Gronowitz S. Wiley; New York: 1991. - 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: 7731 -
3b
Holmes JM.Lee GCM.Wijino M.Weinkam R.Wheeler LA.Garst ME. J. Med. Chem. 1994, 37: 1646 - 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. -
11a
Shevchenko NE.Nenajdenko VG.Balenkova ES. Synthesis 2003, 1191 -
11b
Barbarella G.Melucci M.Sotgiu G. Adv. Mater. 2005, 17: 1581 -
11c
Masui K.Ikegami H.Mori A. J. Am. Chem. Soc. 2004, 126: 5074 -
12a
Zhang H.Yang G.Chen J.Chen Z. Synthesis 2004, 3055 -
12b
Koji S.Satoshi K. Synthesis 1982, 1056 -
12c
Hideo K.Keiichi N.Kazuhiko Y.Hiroo I. Synthesis 1996, 1193 -
13a
Bartolo G.Giuseppe S.Alessia F. Org. Lett. 2000, 2: 351 -
13b
Fazio A.Gabriele B.Salerno G.Destri S. Tetrahedron 1999, 55: 485 -
13c
Ong CW.Chen CM.Wang LF.Shieh PC. Tetrahedron Lett. 1998, 39: 9191 -
13d
Stephensen H.Zaragona F. J. Org. Chem. 1997, 62: 6096 - 14
Gewald K. Angew. Chem. 1961, 73: 114 -
15a
Sommen G.Comel A.Kirsch G. Synlett 2001, 1731 -
15b
Msahraqui SH.Hariharasubrahmanian H.Kumar S. Synthesis 1999, 2030 -
15c
Sommen G.Comel A.Kirsch G. Tetrahedron Lett. 2002, 43: 257 - 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: 923 -
18b
Alizadeh A.Rostamnia S.Hu ML. Synlett 2006, 1592 -
18c
Alizadeh A.Rostamnia S.Zhu LG. Tetrahedron 2006, 62: 5641 -
19a
Alizadeh A.Rostamnia S.Zohreh N.Oskueyan Q. Synlett 2007, 1610 -
19b
Alizadeh A.Rostamnia S.Esmaili AA. Synthesis 2007, 709 -
19c
Alizadeh A.Oskueyan Q.Rostamnia S. Synthesis 2007, 2637 -
20a
Alizadeh A.Hosseinpour R.Rostamnia S. Synthesis 2008, 2462 -
20b
Alizadeh A.Hosseinpour R.Rostamnia S. Synthesis 2008, 3742 - 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: 98 -
22b
Huisgen R.Morikawa M.Herbig K.Brunn E. Chem. Ber. 1967, 100: 1094 -
22c
Winterfeldt E. Chem. Ber. 1965, 98: 3537 -
23a
Zbiral E. Synthesis 1974, 775 -
23b
Becker KB. Tetrahedron 1987, 36: 1717