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 2015; 47(09): 1329-1336
DOI: 10.1055/s-0034-1378687
DOI: 10.1055/s-0034-1378687
paper
Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines
Further Information
Publication History
Received: 03 December 2014
Accepted after revision: 19 January 2015
Publication Date:
24 February 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201509/lookinside/thumbnails/10.1055-s-0034-1378687-1.jpg)
Abstract
The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378687.
- Supporting Information
-
References
- 1a Trofimov BA, Schmidt EYu, Ushakov IA, Zorina NV, Skital’tseva EV, Protsuk NI, Mikhaleva AI. Chem. Eur. J. 2010; 16: 8516
- 1b Trofimov BA, Schmidt EYu, Zorina NV, Ivanova EV, Ushakov IA, Mikhaleva AI. Adv. Synth. Catal. 2012; 354: 1813
- 1c Trofimov BA, Schmidt EYu, Zorina NV, Ivanova EV, Ushakov IA. J. Org. Chem. 2012; 77: 6880
- 1d Schmidt EYu, Zorina NV, Tarasova OA, Ushakov IA, Trofimov BA. Mendeleev Commun. 2013; 23: 204
- 2 Radin NS. Drug Dev. Res. 2008; 69: 15
- 3a Hyde AM, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 177
- 3b Sämann C, Knochel P. Synthesis 2013; 45: 1870
- 3c Mokar BD, Liu R.-S. Chem. Commun. 2014; 50: 8966
- 3d Jadhav AM, Gawade SA, Vasu D, Dateer RB, Liu R.-S. Chem. Eur. J. 2014; 20: 1813
- 4a Ohtsuka Y, Sasahara T, Oishi T. Chem. Pharm. Bull. 1982; 30: 1106 ; and references cited therein
- 4b Gohain M, Gogoi BJ, Prajapati D, Sandhu JS. New J. Chem. 2003; 27: 1038
- 4c Comprehensive Organic Functional Group Transformations II . Katritzky AR, Taylor RJ. K. Elsevier; Amsterdam: 2005
- 4d Iwasaki M, Morita E, Uemura M, Yorimitsu H, Oshima K. Synlett 2007; 167
- 5 Schmidt EYu, Tatarinova IV, Ivanova EV, Zorina NV, Ushakov IA, Trofimov BA. Org. Lett. 2013; 15: 104
- 6 See review: Shaaban MR, Mayhoub AS, Farag AM. Expert Opin. Ther. Patents 2012; 22: 253
- 7a Ali MA, Shaharyar M, Siddiqui AA. Eur. J. Med. Chem. 2007; 42: 268
- 7b Shaharyar M, Siddiqui AA, Ali MA. Bioorg. Med. Chem. Lett. 2006; 16: 4571
- 7c Ali MA, Yar MS, Kumar M, Pandian GS. Nat. Prod. Res. 2007; 21: 575
- 8a Bhat BA, Dhar K, Puri SC, Saxena AK, Shanmugavel M, Qazi GN. Bioorg. Med. Chem. Lett. 2005; 15: 3177
- 8b Shaharyar M, Abdullah MM, Bakht MA, Majeed J. Eur. J. Med. Chem. 2010; 45: 114
- 8c Kobayashi H, Dorai T, Holland JF, Ohnuma T. Cancer Res. 1994; 54: 1271
- 8d Rostom SA. F. Bioorg. Med. Chem. 2006; 14: 6475
- 8e Mazumdar T, DeVecchio J, Agyeman A, Shi T, Houghton JA. Cancer Res. 2011; 71: 5904
- 9a Singh P, Negi JS, Joshi née Pant G, Rawat MS. M. Molbank 2010; M650
- 9b Sid A, Lamara K, Mokhtari M, Ziani N, Mosset P. Eur. J. Chem. 2011; 2: 311
- 10a Insuasty B, Chamizo L, Minoz J, Tigreros A, Quiroga J, Abonia R, Nogueras M, Cobo J. Arch. Pharm. Chem. Life Sci. 2012; 345: 275
- 10b Rostom SA. F. M, Badr H, Abd El Razik HA, Ashour HM. A, Abdel-Wahab AE. Arch. Pharm. Chem. Life Sci. 2011; 344: 572
- 11a Rajput AP, Rajput SS. Int. J. Pharm. Pharm. Sci. 2011; 3: 346
- 11b Hassan SY. J. Braz. Chem. Soc. 2011; 22: 1286
- 11c Dajia B, Srivastava YK. Eur. J. Chem. 2007; 4: 187
- 12a Kendre MM, Baseer MA. Am. J. Adv. Drug Deliv. 2013; 1: 387
- 12b Azarifar D, Shaebanzadeh M. Molecules 2001; 7: 885
- 13 Khalil OM, Refaat HM. Orient. J. Chem. 2011; 27: 1581
- 14 Dimethyl Sulfoxide (DMSO), Technical Bulletin . Crown Zellerbach Chemical Products Division; Vancouver (Orchards) (WA, USA): 1985
- 15 Nagayama K, Kumar A, Wutrich K, Ernst RR. J. Magn. Reson. 1980; 40: 321
- 16 Wagner G, Wutrich K. J. Mol. Biol. 1982; 155: 347
- 17 Bodenhausen G, Ruben D. J. Chem. Phys. Lett. 1980; 69: 185
- 18 Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093
For selected examples, see:
For selected examples, see:
For selected examples, see: