Synthesis of Pyrazoles, Diazepines,
Enaminones, and Enamino Esters Using 12-Tungstophosphoric Acid as
a Reusable Catalyst in Water

Xiang Chen; Jin She; Zhicai Shang; Jun Wu; Haifeng Wu; Peizhi Zhang

doi:10.1055/s-0028-1083169

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Synthesis 2008(21): 3478-3486
DOI: 10.1055/s-0028-1083169

PAPER

Synthesis of Pyrazoles, Diazepines, Enaminones, and Enamino Esters Using 12-Tungstophosphoric Acid as a Reusable Catalyst in Water

Xiang Chen^a, Jin She^a, Zhicai Shang*^a, Jun Wu*^a, Haifeng Wu^a, Peizhi Zhang^b
^a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87952379; e-Mail: shangzc@zju.edu.cn;
^b School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310012, P. R. of China

Further Information

Publication History

Received 4 June 2008
Publication Date:
16 October 2008 (online)

Abstract
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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

References

1a Behr LC. Fusco R. Jarboe CH. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings Wiley RH. Interscience; New York: 1967.

Google Scholar
1b Elguero J. In Comprehensive Heterocyclic Chemistry II Vol. 3: Katritzky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1996. p.1

Google Scholar
1c Mahajan RN. Havaldar FH. Fernandes PS. J. Indian Chem. Soc. 1991, 68: 245

Google Scholar
1d Janus SL. Magdif AZ. Erik BP. Claus N. Monatsh. Chem. 1999, 130: 1167

Google Scholar
2a Edafiogho IO. Moore JA. Alexander MS. Scott KR. J. Pharm. Sci. 1994, 83: 1155

Google Scholar
2b Foster JE. Nicholson JM. Butcher R. Stables JP. Edafiogho IO. Goodwin AM. Henson MC. Smith CA. Scott KR. Bioorg. Med. Chem. 1999, 7: 2415

Google Scholar
2c Michael JP. Koning CB. Hosken GD. Stanbury TV. Tetrahedron 2001, 57: 9635

Google Scholar
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

Crossref Google Scholar
4a Polshettiwar V. Varma RS. Tetrahedron Lett. 2008, 49: 397

Google Scholar
4b Wang Z. Qin H. Green Chem. 2004, 6: 90

Google Scholar
4c Katritzky AR. Handbook of Heterocyclic Chemistry Pergamon; New York: 1985. p.416

Google Scholar
4d Ahmed MSM. Kobayashi K. Mori A. Org. Lett. 2005, 7: 4487

Google Scholar
4e Heller ST. Natarajan SR. Org. Lett. 2006, 8: 2675

Google Scholar
4f Deng X. Mani NS. Org. Lett. 2006, 8: 3505

Google Scholar
4g Armstrong A. Jones LH. Knight JD. Kelsey RD. Org. Lett. 2005, 7: 713

Google Scholar
5 Rault S. Gillard AC. Foloppe MP. Robba M. Tetrahedron Lett. 1995, 36: 6673

Google Scholar
6 Eary CT. Clausen D. Tetrahedron Lett. 2006, 47: 6899

Crossref Google Scholar
7a Wang QF. Hu B. Luo BH. Hu CM. Tetrahedron Lett. 1998, 39: 2377

Google Scholar
7b Bonacorso HG. Lourega RV. Deon ED. Zanatta N. Martins MAP. Tetrahedron Lett. 2007, 48: 4835

Google Scholar
7c Cairns J. Clarkson TR. Hamersma JAM. Rae DR. Tetrahedron Lett. 2002, 43: 1583

Google Scholar
8a Valduga CJ. Braibante HS. Braibante EFJ. J. Heterocycl. Chem. 1998, 35: 189

Google Scholar
8b Rechsteiner B. Texier-Boullet F. Hamalin J. Tetrahedron Lett. 1993, 34: 5071

Google Scholar
8c Braibante MEF. Braibante S. Missio L. Andricopulo A. Synthesis 1994, 898

Google Scholar
8d Arcadi A. Bianchi G. Di Giuseppe S. Marinelli F. Green Chem. 2003, 5: 64

Google Scholar
8e Khosropour AR. Khodaei MM. Kookhazadeh M. Tetrahedron Lett. 2004, 45: 1725

Google Scholar
8f Bartoli G. Bosco M. Locatelli M. Marcantoni E. Melchiorre P. Sambri L. Synlett 2004, 239

Google Scholar
8g Khodaei MM. Khosropour AR. Kookhazadeh M. Synlett 2004, 1980

Google Scholar
8h Das B. Venkateswarlu K. Majhi A. Reddy MR. Reddy KN. Rao YK. Ravikumar K. Sridhar B. J. Mol. Catal. A: Chem. 2006, 246: 276

Google Scholar
9a Chao JL. Chem. Rev. 2005, 105: 3095

Google Scholar
9b Li CJ. Chang TH. Organic Reactions in Aqueous Media Wiley; New York: 1997.

Google Scholar
9c Demko ZP. Sharpless KB. J. Org. Chem. 2001, 66: 7945

Google Scholar
9d Fringuelli F. Pizzo F. Tortoioli S. Vaccaro L. Org. Lett. 2005, 7: 4411

Google Scholar
9e Pirrung MC. Sarma KD. J. Am. Chem. Soc. 2004, 126: 444

Google Scholar
9f Azoulay S. Manabe K. Kobayashi S. Org. Lett. 2005, 7: 4593

Google Scholar
9g Manabe K. Limura S. Sun X.-M. Kobayashi S. J. Am. Chem. Soc. 2002, 124: 11971

Google Scholar
10a Heravi MM. Derikvand F. Bamoharram FF. J. Mol. Catal. A: Chem. 2005, 242: 173

Google Scholar
10b Azizi N. Torkiyan L. Saidi MR. Org. Lett. 2006, 8: 2079

Google Scholar
10c Yadav JS. Subba Reddy BV. Sridhar P. Reddy JSS. Nagaiah K. Lingaiah N. Saiprasad PS. Eur. J. Org. Chem. 2004, 552

Google Scholar
10d Kozhevnikov IV. Catal. Rev. Sci. Eng. 1995, 37: 311

Google Scholar
10e Mison M. Noriji N. Appl. Catal. 1990, 64: 1

Google Scholar
10f Izumi Y. Hasebe R. Urabe K. J. Catal. 1983, 84: 402

Google Scholar
10g Soeda H. Okuara T. Misono M. J. Mol. Chem. Lett. 1994, 909

Google Scholar
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: 7702

Google Scholar
11b Okuhara T. Nishimura T. Watanabe H. Misono M. J. Mol. Catal. 1992, 74: 247

Google Scholar
12a Butler RN. Hanniffy JM. Stephens JC. Burke LA. J. Org. Chem. 2008, 73: 1354

Google Scholar
12b Chambers D. Denny WA. Buckleton JS. Clark GR. J. Org. Chem. 1985, 50: 4736

Google Scholar
12c Dvorak CA. Rudolph DA. Ma S. Carruthers NI. J. Org. Chem. 2005, 70: 4188

Google Scholar
12d Han B. Liu Z. Liu Q. Yang L. Liu Z.-L. Yu W. Tetrahedron 2006, 62: 2492

Google Scholar
12e Texier-Boullet F . Klein B . Hamelin J . Synthesis 1986, 409

Google Scholar
12f Bieringer S. Holzer W. Heterocycles 2006, 68: 1825

Google Scholar
12g Gholap AR. Chakor NS. Daniel T. Lahoti RJ. Srinivasan KV. J. Mol. Catal. A: Chem. 2006, 245: 37

Google Scholar
12h Zhang Z.-H. Yin L. Wang Y.-M. Adv. Synth. Catal. 2006, 348: 184

Google Scholar
12i González-Nogal AM. Calle M. Cuadrado P. Eur. J. Org. Chem. 2007, 36: 6089

Google Scholar