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Synthesis 2002(1): 0079-0082
DOI: 10.1055/s-2002-19310
DOI: 10.1055/s-2002-19310
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of Polysubstituted 3-Halo-2(1H)-Pyridinones
Further Information
Received
27 July 2001
Publication Date:
04 August 2004 (online)
Publication History
Publication Date:
04 August 2004 (online)
Abstract
A series of 3-halo-2(1H)-pyridinones 4 have been synthesized by treatment of δ-dienaminoesters 1 with N-halosuccinimide in basic medium. The chemoselectivity of the reaction is discussed.
Key words
pyridinones - pyrroles - δ-dienaminoesters
- 1
Katritzky AR.Rees CW.Scriven EFV. In Comprehensive Heterocyclic Chemistry Vol. 5: Pergamon Press; Oxford: 1996. - 2
Dolle RE.Nicolaou KC. J. Am. Chem. Soc. 1985, 107: 1691 - 3
Cox RJ.O’Hagan D. J. Chem. Soc., Perkin Trans 1 1991, 2537 - 4
Pierce JB.Ariyan ZS.Ovenden GS. J. Med. Chem. 1982, 25: 131 -
5a
Marcoux JF.Marcotte FA.Wu J.Dormer PG.Davies IW.Hughes D.Reider PJ. J. Org. Chem. 2001, 66: 4194 -
5b
Sieburth SM.Hiel G.Lin CH.Kuan DP. J. Org. Chem. 1994, 59: 80 -
5c
Sieburth SM.Chen J. J. Am. Chem. Soc. 1991, 113: 8163 -
5d
Cainelli G.Panunzio M.Giacomini D.Di Simone B.Camerini R. Synthesis 1994, 805 -
5e
Tutonda MG.Vandenberghe SM.Van Aken KJ.Hoornaert GJ. J. Org. Chem. 1992, 57: 2935 -
5f
Zhang S.Liebeskind LS. J. Org. Chem. 1999, 64: 4042 -
5g
Padwa A.Sheehan SM.Straub CS. J. Org. Chem. 1999, 64: 8648 -
6a
Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508 -
6b
Choi WB.Houpis IN.Churchill H.Molina O.Lynch JE.Volante RP.Reider PJ.King AO. Tetrahedron Lett. 1995, 36: 4571 -
6c
Houpis IN.Choi WB.Reider PJ.Molina O.Churchill H.Lynch J.Volante RP. Tetrahedron Lett. 1994, 35: 9355 - 7
Domagala JM. J. Heterocyclic Chem. 1984, 21: 1705 - 8
Agami C.Dechoux L.Hebbe S. Synlett 2001, 1440 - For cyclizations of dehalogenated δ-dienaminoesters see
-
9a
Anghelide N.Draghici C.Raileanu D. Tetrahedron 1974, 30: 623 -
9b
Palacios F.Garcia J.Ochoa de Retana A.Oyarzabal J. Heterocycles 1995, 41: 1915 -
9c
Cocco MT.Congiu C.Maccioni A.Onnis V. Synthesis 1992, 371 -
9d
Lee CH.Kohn H. J. Heterocycl. Chem. 1990, 27: 2107 -
9e
Khan MA.Adams H. Tetrahedron Lett. 1999, 40: 5389 - 3-Bromo-2(1H)-pyridinone(4a) has been correlated with methyl-6-hydroxynicotinate. By hydrogenolysis compound 4a under atmospheric pressure using Pd/C as catalyst methyl-6-hydroxynicotinate was obtained. See:
-
10a
Shiao MJ.Ku WS.Hwu JR. Heterocycles 1993, 36: 323 -
10b
Torrado A.Imperiali A. J. Org. Chem. 1996, 61: 8940