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Synthesis 2003(14): 2211-2215
DOI: 10.1055/s-2003-42085
DOI: 10.1055/s-2003-42085
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Convergent Synthesis of 4,4′-Bispyridyl-5,5′-Disubstituted-2,2-Bisoxazoles and -Bisthiazoles
Further Information
Received
28 May 2003
Publication Date:
24 September 2003 (online)
Publication History
Publication Date:
24 September 2003 (online)
Abstract
A convergent strategy for the synthesis of 4,4′-bispyridyl-5,5′-disubstituted-2,2′-bisoxazoles and -bisthiazoles from diamides has been achieved.
Key words
heterocycles - amides - oxazoles - thiazoles - fluorine
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1a
Smith AB.Minbiole KP.Freeze S. Synlett 2001, 1739 ; and references therein -
1b
Cardwell SK.Hermitage SA.Sjolin A. Tetrahedron Lett. 2000, 41: 4239 ; and references therein - 2
Hernández-Alcoceba L.Saniger J.Campos F.Núñez MC.Khaless MA.Gallo A.Espinosa A.Lacal JC. Oncogene 1997, 15: 2289 -
3a
Li J.Jeong S.Esser L.Harran PG. Angew. Chem. Int. Ed. 2001, 40: 4765 -
3b
Li J.Burgett AWG.Esser L.Amezcua C.Harran PG. Angew. Chem. Int. Ed. 2001, 40: 4770 -
3c
Magnus P.McIver EG. Tetrahedron Lett. 2000, 41: 831 -
4a
Doyle KJ.Moody CJ. Tetrahedron Lett. 1992, 33: 7769 -
4b
Singh SP.Naithami R.Aggarwal R.Prakash O. Synth. Commun. 2001, 31: 3747 - 5
Chittari P.Hamada Y.Shioiri T. Synlett 1998, 1022 ; and references therein - 6
Williams DR.Brooks DA.Meyer KG. Tetrahedron Lett. 1998, 39: 8023 - 7
Schröeder R.Schöllkopf U.Blume E.Hoppe I. Liebigs Ann. Chem. 1975, 533 - 8
Burger K.Hülb D.Geith K. Synthesis 1988, 36: 199 - 9
Burger K.Hülb D.Geith K. Synthesis 1988, 36: 194 - 10
Helmreich B,Burger K,Maier G,Hecht R, andNuyken O. inventors; U.S. Patent 5300625. - 11
Braña MF.Castellano JM.de Miguel P.Posada P.Sanz CR.Migallón AS. Tetrahedron 1994, 50: 10061 - General procedures used for synthesis of diamides 4:
-
12a For Z = (CH3)2C, p,p′-PhOPh, p,p′-PhC(CF3)2Ph, see:
Bernasconi S.Comini A.Corbella A.Gariboldi P.Sisti M. Synthesis 1980, 385 -
12b For Z = p-phenyl, p-biphenyl, oxalyl, CH2CH2, see:
Tamiz AP.Cai SX.Zhou ZL.Yuen PW.Schelkun RM.Whittemore ER.Weber E.Woodward RM.Keana JFW. J. Med. Chem. 1999, 42: 3412 -
15a
Funabiki K.Noma N.Kuzuya G.Matsui M.Shibata K. J. Chem. Res., Synop. 1999, 300 ; and references therein -
15b
Filler R. In Organofluorine and their Industrial ApplicationBanks RE. Ellis Horwood; Chichester: 1979. -
16a
Kawase M.Saito S.Kikuchi H.Miyamae H. Heterocycles 1997, 45: 2185 -
16b
Kawase M. Tetrahedron Lett. 1994, 35: 149 -
16c
Kawase M. Heterocycles 1993, 36: 2441 -
16d
Kawase M.Miyamae H.Narita M.Kurihara T. Tetrahedron Lett. 1993, 34: 859
References
See experimental for typical procedure for the synthesis of anhydrobases 5.
14See experimental for representative example of analytical data of compounds 5.
17See experimental for preparation of dithioamides 6, and representative example of analytical data.