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Synthesis 2004(11): 1744-1746
DOI: 10.1055/s-2004-829149
DOI: 10.1055/s-2004-829149
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Silica-Supported 1,3-Dibromo-5,5-dimethylhydantoin (DBH) as a Useful Reagent for Microwave-Assisted Aromatization of 1,3,5-Trisubstituted Pyrazolines under Solvent-Free Conditions
Further Information
Received
16 March 2004
Publication Date:
13 July 2004 (online)
Publication History
Publication Date:
13 July 2004 (online)
Abstract
1,3,5-Trisubstituted pyrazolines are rapidly and conveniently oxidized to their corresponding pyrazoles by 1,3-dibromo-5,5-dimethylhydantoin (DBH) under microwave irradiation and solvent-free conditions. The presence of silica gel as a supporting agent is shown to be effective in reducing the reaction times and increasing the yields.
Key words
pyrazolines - 1,3-dibromo-5,5-dimethylhydantoin (DBH) - aromatization - solid-surface - microwave irradiation
-
1a
Caddick S. Tetrahedron 1995, 52: 1403 -
1b
Varma RS. Green Chem. 1999, 1: 43 -
1c
Majetich M.Hicks RJ. Microwave Power Electromagn. Energy 1995, 30: 27 -
1d
Gupta R.Gupta AK.Paul S.Kachroo P. Ind. J. Chem. 1995, 34B: 151 -
2a
Mckillop A.Young DW. Synthesis 1979, 401 -
2b
Mckillop A.Young DW. Synthesis 1979, 481 -
2c
Posner GH. Angew. Chem., Int. Ed. Engl. 1978, 17: 487 ; Angew. Chem. 1978, 90, 527 -
2d
Balogh M.Laszlo P. Organic Chemistry Using Clays Springer Verlag; Berlin: 1993. -
2e
Clark JH. Catalysis of Organic Reactions by Supported Inorganic Reagents VCH; Weinheim: 1994. -
3a
Caddick S. Tetrahedron 1995, 51: 10403 -
3b
Strauss CR.Trainor RW. Aust. J. Chem. 1995, 48: 1665 -
3c
Marreto-Terrero AL.Loupy A. Synlett 1996, 245 -
3d
Varma RS. In Microwave-Assisted Reactions under Solvent-Free Dry Conditions in Microwaves, Theory and Application in Material Processing IV Vol. 80:Clark D.Sutton W.Lewis D. American Ceramic Society, Ceramic Transactions; New York: 1997. p.357-365 -
4a
Takabata E.Kodama R.Tanaka Y.Dohmori R.Tachizawa H.Naita T. Chem. Pharm. Bull. 1979, 16: 1900 -
4b
Parmar SS.Pandy BR.Dwivedi C.Harbison RD. J. Pharm. Sci. 1974, 63: 1152 -
5a
Azarifar D.Shaebanzadeh M. Moleclues 2002, 7: 885 -
5b
Azarifar D.Ghasemnejad H. Molecules 2003, 8: 642 - 6
Sabita G.Reddy GSK.Reddy CS.Fatima N.Yadav JS. Synthesis 2003, 1267 - 7
Nakamichi N.Kawashita Y.Hayashi M. Org. Lett. 2002, 4: 3955 - 8
Shah JN.Shah CK. J. Org. Chem. 1978, 43: 1266 - 9
Singh SP.Kumar D.Prakash O.Kapoor RP. Synth. Commun. 1997, 27: 2683 - 10
Gladstone WAF.Norman ROC. J. Chem. Soc., Chem. Commun. 1966, 1536 - 11
Bhatnager I.George MV. Tetrahedron 1968, 24: 1293 - 12
Smith LI.Howard KL. J. Am. Chem. Soc. 1943, 65: 159 - 13
Ried W.Lantzsch R. Chem. Ber. 1969, 102: 378 -
14a
Tanaka K.Toda F. Chem. Rev. 2000, 100: 1025 -
14b
Krchnak V.Holladay MW. Chem. Rev. 2002, 102: 61