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Synlett 2003(5): 0711-0713
DOI: 10.1055/s-2003-38369
DOI: 10.1055/s-2003-38369
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York
Solid-Phase Synthesis of Heterocycles from 1,4-Diketone Synthons [1]
Further Information
Received
6 November 2002
Publication Date:
28 March 2003 (online)
Publication History
Publication Date:
28 March 2003 (online)

Abstract
The solid-phase synthesis of furans, thiophenes, pyrroles and pyridazines from 1,4-diketones as the common intermediate is reported. A diverse collection of these heterocyclic compounds is readily prepared in two high yielding steps.
Key words
1,4-diketones - furans - pyrroles - thiophenes - pyridazines
IICT communication No. 020814
-
2a
Nefzi A.Ostresh JM.Houghten RA. Chem. Rev. 1997, 97: 449 -
2b
Krchnak V.Holladay MW. Chem. Rev. 2002, 102: 61 - 3
Raghavan S.Anuradha K. Tetrahedron Lett. 2002, 43: 5181 - For earlier reports on the solid-phase synthesis of furans refer:
-
4a
Gowravaram MR.Gallop MA. Tetrahedron Lett. 1996, 37: 6973 -
4b
Whitehouse DL.Nelson KH.Savinov SN.Austin DJ. Tetrahedron Lett. 1997, 38: 7139 -
4c
Han Y.Roy A.Giroux A. Tetrahedron Lett. 2000, 41: 5447 - 5 For an earlier report on the solid-phase
synthesis of thiophene refer:
Han Y.Giroux A.Lepine C.Laliberte F.Huang Z.Perrier H.Bayly C.Young R. Tetrahedron 1999, 55: 11669 - 6 For an earlier report on the solid-phase
synthesis of pyrroles refer:
Mjalli AMM.Toyonaga BE. In Molecular Diversity and Combinatorial Chemistry: Libraries and Drug DiscoveryChaiken IM.Janda KD. American Chemical Society; Washington DC: 1996. p.70 - 7
Friedrischsen W.Pagel K. Prog. Heterocycl. Chem. 1995, 7: 130 -
8a
Di Santo R.Costi R.Artico M.Massa S.Lampis G.Deidda D.Rompei R. Biorog. Med. Chem. Lett. 1998, 8: 2931 -
8b
Ragno R.Marshall GR.Di Santo R.Costi R.Massa S.Rompei R.Artico M. Bioorg. Med. Chem. 2000, 8: 1423 -
9a
Saltiel E.Ward A. Drugs 1987, 34: 222 -
9b
Aubert D,Ferrand C, andMaffrand JP. inventors; EP 99802. ; Chem. Abstr. 1984, 100, 191856z -
10a
Frank H.Heinisch G. Pharmacologically active pyridazines Part I. In Progress in medicinal chemistryEllis GP.West GB. Elsevier; Amsterdam: 1990. Vol. 27. -
10b
Curran WV.Ross A. J. Med. Chem. 1974, 17: 273 - 11
Drewes SE.Hogan CJ. Synth. Commun. 1989, 19: 2101 - 12
Brain CT.Brunton SA. Synlett 2001, 382 - 13
Shridhar DR.Jogibhukta M.Shantan Rao P.Handa VK. Synthesis 1982, 1061 - 14
Demir AS.Akmedov IM.Sesenouglu O.Alpturk O.Apaydm S.Gercek Z.Ibrahimzade N. J. Chem. Soc., Perkin Trans. 1 2001, 1162 ; and references cited therein - 15
Stetter H.Friederich J. Chem. Ber. 1981, 114: 564
References
IICT communication No. 020814