Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(21): 3478-3486
DOI: 10.1055/s-0028-1083169
DOI: 10.1055/s-0028-1083169
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Pyrazoles, Diazepines, Enaminones, and Enamino Esters Using 12-Tungstophosphoric Acid as a Reusable Catalyst in Water
Further Information
Received
4 June 2008
Publication Date:
16 October 2008 (online)
Publication History
Publication Date:
16 October 2008 (online)

Abstract
12-Tungstophosphoric acid (H3PW12O40) is found to be an efficient and recyclable catalyst in promoting a chemo- and regioselective condensation of hydrazines/hydrazides, diamines, and primary amines with various 1,3-dicarbonyl compounds in pure water at room temperature to afford pyrazoles, diazepines, and enaminones/enamino esters, respectively, in high yields.
Key words
12-tungstophosphoric acid - recyclable catalyst - condensation - 1,3-dicarbonyl compounds - aqueous medium
- 1a
Behr LC.Fusco R.Jarboe CH. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed RingsWiley RH. Interscience; New York: 1967.MissingFormLabel - 1b
Elguero J. In Comprehensive Heterocyclic Chemistry II Vol. 3:Katritzky AR.Rees CW.Scriven EF. Pergamon; Oxford: 1996. p.1MissingFormLabel - 1c
Mahajan RN.Havaldar FH.Fernandes PS. J. Indian Chem. Soc. 1991, 68: 245MissingFormLabel - 1d
Janus SL.Magdif AZ.Erik BP.Claus N. Monatsh. Chem. 1999, 130: 1167MissingFormLabel - 2a
Edafiogho IO.Moore JA.Alexander MS.Scott KR. J. Pharm. Sci. 1994, 83: 1155MissingFormLabel - 2b
Foster JE.Nicholson JM.Butcher R.Stables JP.Edafiogho IO.Goodwin AM.Henson MC.Smith CA.Scott KR. Bioorg. Med. Chem. 1999, 7: 2415MissingFormLabel - 2c
Michael JP.Koning CB.Hosken GD.Stanbury TV. Tetrahedron 2001, 57: 9635MissingFormLabel - 3
Michael JP.Koning CB.Gravestock D.Hosken GD.Howard AS.Jungmann CM.Krause RWM.Parson AS.Pelly SC.Stanbury TV. Pure Appl. Chem. 1999, 71: 979 - 4a
Polshettiwar V.Varma RS. Tetrahedron Lett. 2008, 49: 397MissingFormLabel - 4b
Wang Z.Qin H. Green Chem. 2004, 6: 90MissingFormLabel - 4c
Katritzky AR. Handbook of Heterocyclic Chemistry Pergamon; New York: 1985. p.416MissingFormLabel - 4d
Ahmed MSM.Kobayashi K.Mori A. Org. Lett. 2005, 7: 4487MissingFormLabel - 4e
Heller ST.Natarajan SR. Org. Lett. 2006, 8: 2675MissingFormLabel - 4f
Deng X.Mani NS. Org. Lett. 2006, 8: 3505MissingFormLabel - 4g
Armstrong A.Jones LH.Knight JD.Kelsey RD. Org. Lett. 2005, 7: 713MissingFormLabel - 5
Rault S.Gillard AC.Foloppe MP.Robba M. Tetrahedron Lett. 1995, 36: 6673 - 6
Eary CT.Clausen D. Tetrahedron Lett. 2006, 47: 6899 - 7a
Wang QF.Hu B.Luo BH.Hu CM. Tetrahedron Lett. 1998, 39: 2377MissingFormLabel - 7b
Bonacorso HG.Lourega RV.Deon ED.Zanatta N.Martins MAP. Tetrahedron Lett. 2007, 48: 4835MissingFormLabel - 7c
Cairns J.Clarkson TR.Hamersma JAM.Rae DR. Tetrahedron Lett. 2002, 43: 1583MissingFormLabel - 8a
Valduga CJ.Braibante HS.Braibante EFJ. J. Heterocycl. Chem. 1998, 35: 189MissingFormLabel - 8b
Rechsteiner B.Texier-Boullet F.Hamalin J. Tetrahedron Lett. 1993, 34: 5071MissingFormLabel - 8c
Braibante MEF.Braibante S.Missio L.Andricopulo A. Synthesis 1994, 898MissingFormLabel - 8d
Arcadi A.Bianchi G.Di Giuseppe S.Marinelli F. Green Chem. 2003, 5: 64MissingFormLabel - 8e
Khosropour AR.Khodaei MM.Kookhazadeh M. Tetrahedron Lett. 2004, 45: 1725MissingFormLabel - 8f
Bartoli G.Bosco M.Locatelli M.Marcantoni E.Melchiorre P.Sambri L. Synlett 2004, 239MissingFormLabel - 8g
Khodaei MM.Khosropour AR.Kookhazadeh M. Synlett 2004, 1980MissingFormLabel - 8h
Das B.Venkateswarlu K.Majhi A.Reddy MR.Reddy KN.Rao YK.Ravikumar K.Sridhar B. J. Mol. Catal. A: Chem. 2006, 246: 276MissingFormLabel - 9a
Chao JL. Chem. Rev. 2005, 105: 3095MissingFormLabel - 9b
Li CJ.Chang TH. Organic Reactions in Aqueous Media Wiley; New York: 1997.MissingFormLabel - 9c
Demko ZP.Sharpless KB. J. Org. Chem. 2001, 66: 7945MissingFormLabel - 9d
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Org. Lett. 2005, 7: 4411MissingFormLabel - 9e
Pirrung MC.Sarma KD. J. Am. Chem. Soc. 2004, 126: 444MissingFormLabel - 9f
Azoulay S.Manabe K.Kobayashi S. Org. Lett. 2005, 7: 4593MissingFormLabel - 9g
Manabe K.Limura S.Sun X.-M.Kobayashi S. J. Am. Chem. Soc. 2002, 124: 11971MissingFormLabel - 10a
Heravi MM.Derikvand F.Bamoharram FF. J. Mol. Catal. A: Chem. 2005, 242: 173MissingFormLabel - 10b
Azizi N.Torkiyan L.Saidi MR. Org. Lett. 2006, 8: 2079MissingFormLabel - 10c
Yadav JS.Subba Reddy BV.Sridhar P.Reddy JSS.Nagaiah K.Lingaiah N.Saiprasad PS. Eur. J. Org. Chem. 2004, 552MissingFormLabel - 10d
Kozhevnikov IV. Catal. Rev. Sci. Eng. 1995, 37: 311MissingFormLabel - 10e
Mison M.Noriji N. Appl. Catal. 1990, 64: 1MissingFormLabel - 10f
Izumi Y.Hasebe R.Urabe K. J. Catal. 1983, 84: 402MissingFormLabel - 10g
Soeda H.Okuara T.Misono M. J. Mol. Chem. Lett. 1994, 909MissingFormLabel - Among heteropolyacids, tungstic acids are the most widely used catalysts owing to their high acid strengths, thermal stabilities and low reducibilities. The acidity strength follows the order: H3PW12O40 > 4-MeC6H4SO3H > H2SO4, which can be found in:
- 11a
Drago RS.Dias JA.Maier TO. J. Am. Chem. Soc. 1997, 119: 7702MissingFormLabel - 11b
Okuhara T.Nishimura T.Watanabe H.Misono M. J. Mol. Catal. 1992, 74: 247MissingFormLabel - 12a
Butler RN.Hanniffy JM.Stephens JC.Burke LA. J. Org. Chem. 2008, 73: 1354MissingFormLabel - 12b
Chambers D.Denny WA.Buckleton JS.Clark GR. J. Org. Chem. 1985, 50: 4736MissingFormLabel - 12c
Dvorak CA.Rudolph DA.Ma S.Carruthers NI. J. Org. Chem. 2005, 70: 4188MissingFormLabel - 12d
Han B.Liu Z.Liu Q.Yang L.Liu Z.-L.Yu W. Tetrahedron 2006, 62: 2492MissingFormLabel - 12e
Texier-Boullet F .Klein B .Hamelin J . Synthesis 1986, 409MissingFormLabel - 12f
Bieringer S.Holzer W. Heterocycles 2006, 68: 1825MissingFormLabel - 12g
Gholap AR.Chakor NS.Daniel T.Lahoti RJ.Srinivasan KV. J. Mol. Catal. A: Chem. 2006, 245: 37MissingFormLabel - 12h
Zhang Z.-H.Yin L.Wang Y.-M. Adv. Synth. Catal. 2006, 348: 184MissingFormLabel - 12i
González-Nogal AM.Calle M.Cuadrado P. Eur. J. Org. Chem. 2007, 36: 6089MissingFormLabel