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Synthesis 2013; 45(6): 830-836
DOI: 10.1055/s-0032-1316856
DOI: 10.1055/s-0032-1316856
paper
Facile One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles from Propargylic Alcohols via Propargyl Hydrazides
Further Information
Publication History
Received: 17 December 2012
Accepted after revision: 25 January 2013
Publication Date:
08 February 2013 (online)
Abstract
A new and efficient metal-free, two-component, one-pot approach to a variety of 3,5-disubstituted 1H-pyrazoles has been developed from propargylic alcohols. This transformation proceeds via an acid-catalyzed propargylation of N,N-diprotected hydrazines followed by base-mediated 5-endo-dig cyclization leading to 3,5-disubstituted 1H-pyrazoles in good overall yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Chimenti F, Fioravanti R, Bolasco A, Manna F, Chimenti P, Secci D, Befani O, Turini P, Ortuso F, Alcaro S. J. Med. Chem. 2007; 50: 425
- 1b Elguero J, Goya P, Jagerovic N, Silva AM. S. Targets Heterocycl. Syst. 2002; 6: 52
- 1c Elguero J In Comprehensive Heterocyclic Chemistry . Vol. 5. Katrizky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996
- 2 For a recent review, see: Fustero S, Sanchez-Roselle M, Barrio P, Simen-Fuentes A. Chem. Rev. 2011; 111: 6984
- 3a Peruncheralathan S, Khan TA, Ila H, Junjappa H. J. Org. Chem. 2005; 70: 10030
- 3b Patel MV, Bell R, Majest S, Henry R, Kolasa T. J. Org. Chem. 2004; 69: 7058
- 3c Knorr L. Ber. Dtsch. Chem. Ges. 1883; 16: 2587
- 4 Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Padwa A, Pearson WH. John & Wiley Sons; New York: 2002
- 5a Janin YL. Chem. Rev. 2012; 112: 3924
- 5b Wu L.-L, Ge YC, He T, Zhang L, Fu XL, Fu H.-Y, Chen H, Li R.-X. Synthesis 2012; 44: 1577
- 5c Borkin DA, Puscau M, Carlson A, Solan A, Wheeler KA, Torok B, Dembinski R. Org. Biomol. Chem. 2012; 10: 4505
- 5d Jackowski O, Lecourt T, Micouin L. Org. Lett. 2011; 13: 5664
- 5e Shan G, Liu P, Rao Y. Org. Lett. 2011; 13: 1746
- 5f Babinski DJ, Aguilar HR, Still R, Frantz DE. J. Org. Chem. 2011; 76: 5915
- 5g Willy B, Muller TJ. J. Org. Lett. 2011; 13: 2082
- 5h Verma D, Mobin S, Namboothiri IN. N. J. Org. Chem. 2011; 76: 4764
- 5i Zora M, Kivrak A. J. Org. Chem. 2011; 76: 9379
- 5j Okitsu T, Sato K, Wada A. Org. Lett. 2010; 12: 3506
- 5k Deng X, Mani NS. Org. Lett. 2008; 10: 1307
- 5l Outirite M, Lebrini M, Lagrenee M, Bentiss F. J. Heterocycl. Chem. 2008; 45: 503
- 5m Martin R, Rivero MR, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 7079
- 6a Guillena G, Ramon DJ, Yus M. Chem. Rev. 2010; 110: 1611
- 6b Bandini M, Tragni M. Org. Biomol. Chem. 2009; 7: 1501
- 6c Zeni G, Larock RC. Chem. Rev. 2004; 104: 2285
- 8a Yoshimatsu M, Watanabe H, Koketsu E. Org. Lett. 2010; 12: 4192
- 8b Fang C, Pang Y, Forsyth CJ. Org. Lett. 2010; 12: 4528
- 8c Srihari P, Bhunia DC, Sreedhar P, Mandal SS, Reddy JS. S, Yadav JS. Tetrahedron Lett. 2007; 48: 8120
- 8d Sherry BD, Radosevich AT, Toste FD. J. Am. Chem. Soc. 2003; 125: 6076
- 8e Zhu Y, Yin G, Hong D, Lu P, Wang Y. Org. Lett. 2011; 13: 1024
- 8f Yin G, Zhu Y, Zhang L, Lu P, Wang Y. Org. Lett. 2011; 13: 940
- 8g Yan W, Wang Q, Chen Y, Petersen JL, Shi X. Org. Lett. 2010; 12: 3308
- 8h Reddy ChR, Jithender E, Krishna G, Reddy GV, Jagadeesh B. Org. Biomol. Chem. 2011; 9: 3940
- 8i Zhang M, Yang H, Cheng Y, Zhu Y, Zhu C. Tetrahedron Lett. 2010; 51: 1176
- 8j Chatterjee PN, Roy S. J. Org. Chem. 2010; 75: 4413
- 8k Sanz R, Martinez A, Alvarez-Gutierez JM, Rodriguez F. Eur. J. Org. Chem. 2006; 1383
- 9a Liu P, Deng C.-L, Lei X, Lin G. Eur. J. Org. Chem. 2011; 7308
- 9b Debleds O, Gayon E, Vrancken E, Campagne J.-M. Beilstein J. Org. Chem. 2011; 7: 866
- 9c Sanz R, Miguel D, Gohain M, Garcia-Garcia P, Fernandez-Rodriguez MA, Gonzalez-Perez A, Nieto-Faza O, de Lera AR, Rodriguez F. Chem. Eur. J. 2010; 16: 9818
- 9d Debleds O, Gayon E, Ostaszuk E, Vrancken E, Campagne J.-M. Chem. Eur. J. 2010; 16: 12207
- 9e Berger S, Haak E. Tetrahedron Lett. 2010; 51: 6630
- 9f Gayon E, Debleds O, Nicouleau M, Lamaty F, van der Lee A, Vrancken E, Campagne J.-M. J. Org. Chem. 2010; 75: 6050
- 9g Egi M, Azechi K, Akai S. Org. Lett. 2009; 11: 5002
- 10a Reddy ChR, Vijaykumar J, Jithender E, Reddy GP. K, Gree R. Eur. J. Org. Chem. 2012; 5767
- 10b Reddy ChR, Krishna G, Kavitha N, Latha B, Shin D.-S. Eur. J. Org. Chem. 2012; 5381
- 10c Reddy ChR, Radhika TP, Kumar S, Chandrasekhar S. Eur. J. Org. Chem. 2011; 5967
- 10d Reddy ChR, Vijaykumar J, Gree R. Synthesis 2010; 3715
- 11a Yoshimatsu M, Ohta K, Takahashi N. Chem. Eur. J. 2012; 18: 15602
- 11b Xu S.-X, Hao L, Wang T, Ding Z.-C, Zhan Z.-P. Org. Biomol. Chem. 2013; 11: 294
- 12a Yamamoto H, Yamasaki N, Yoshidome S, Sasaki I, Namba K, Imagawa H, Nishizawa M. Synlett 2012; 23: 1069
- 12b Namba K, Shoji I, Nishizawa M, Tanino K. Org. Lett. 2009; 11: 4970
- 13a Lettan II RB, Scheidt KA. Org. Lett. 2005; 7: 3227
- 13b Huang H, Jiang H, Cao H, Zhao J, Shi D. Tetrahedron 2012; 68: 3135
- 13c Wilson EE, Oliver AG, Hughes RP, Ashfeld BL. Organometallics 2011; 30: 5214
- 13d Kitazume T, Kasai K. Green Chem. 2001; 3: 30
- 13e Downey CW, Mahoney BD, Lipari VR. J. Org. Chem. 2009; 74: 2904
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