RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(15): 2188-2192
DOI: 10.1055/s-0033-1338923
DOI: 10.1055/s-0033-1338923
paper
Direct Electrophilic Acylation of N-Substituted Pyrazoles by Anhydrides of Carboxylic Acids
Weitere Informationen
Publikationsverlauf
Received: 10. März 2013
Accepted after revision: 30. April 2013
Publikationsdatum:
12. Juni 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201315/lookinside/thumbnails/10.1055-s-0033-1338923-1.jpg)
Abstract
A simple, convenient and scalable approach to 1-substituted 4-acylpyrazoles through direct acylation of pyrazoles by anhydrides of aliphatic, aromatic and fluorinated carboxylic acids in the presence of concentrated sulfuric acid as a catalyst is described. Target ketones were obtained in 41–86% isolated yields in high purity without laborious purification. The scope and limitations of the method are discussed.
-
References
- 1a Kurihara T, Uno T, Sakamoto Y. J. Heterocycl. Chem. 1980; 17: 231
- 1b Naito H, Ohsuki S, Atsumi R, Minami M, Mochizuki M, Hirotani K, Kumazawa E, Ejima A. Chem. Pharm. Bull. 2005; 53: 153
- 1c Ralph JM, Faitg TH, Silva DJ, Feng Y, Blackledge CW, Adams JL. Tetrahedron Lett. 2009; 50: 1377
- 1d See, for example, references 6–8 and 15.
- 2a Balbiano L. Gazz. Chim. Ital. 1889; 19: 131
- 2b von Auwers K, Mauss H. J. Prakt. Chem. 1927; 117: 331
- 3 Shvartsberg MS, Vasilevskii SF, Kostrovskii VG, Kotlyarevskii IL. Chem. Heterocycl. Compd. 1969; 5: 797
- 4 Kano K, Scarpetti D, Warner JC, Anselme J.-P, Springer JH, Arison BH. Can. J. Chem. 1986; 64: 2211
- 5 Usami Y, Watanabe R, Fujino Y, Yoneyama H, Harusawa S, Ichikawa H, Shibano M, Ishida C. Chem. Pharm. Bull. 2012; 60: 1550
- 6 Merkul E, Dohe J, Gers C, Mueller TJ. J, Rominger F. Angew. Chem. Int. Ed. 2011; 50: 2966
- 7 Calabrese AA, Duncton MA. J, Futatsugi K, Hirano M, Nagayama S. Pat. Appl. WO 2008059370, 2008 ; Chem. Abstr. 2008, 148, 585892.
- 8 Helal CJ, Chappie TA, Hymphrey JM, Verhoerst PR, Yang E. Pat. Appl. US 20120214791, 2012 ; Chem. Abstr. 2012, 157, 410336.
- 9 Kanaya N, Ishiyama T, Muto R, Watanabe T, Ochiai Y. Pat. Appl. WO 2006004027, 2006 ; Chem. Abstr. 2006, 144, 128970.
- 10 Timmermans PB. M. W. M, Uijttewaal AP, Habraken CL. J. Heterocycl. Chem. 1972; 9: 1373
- 11 Menichi G, Boutar M, Kokel B, Takagi K, Hubert-Habart M. J. Heterocycl. Chem. 1986; 23: 275
- 12 Nagarajan K, Arya VP, Shenoy SJ. J. Chem. Res., Miniprint 1986; 5: 1401
- 13 Alinezhad H, Tajbakhsh M, Zare M. J. Fluorine Chem. 2011; 132: 995
- 14 Taydakov IV, Krasnoselskiy SS. J. Heterocycl. Chem. 2012; 49: 1422
- 15 Mal’tseva SP, Bychkov NN, Stepanov BI, Mushii RYa, Seraya VI. Trudy Instituta - Moskovskii Khimiko-Tekhnologicheskii Institut imeni D. I. Mendeleeva (in Russian) 1974; 80: 56 ; Chem. Abstr. 1976, 85, 62988
- 16 A similar reaction was reported for two isomeric 1-(n-propyl)-3(5)-methyl pyrazoles and Ac2O without any references to previously published results, see: Attaryan OS, Khachatryan SF. Hayastani Kimiakan Handes (in Russian and Armenian) 2007; 60: 94 ; Chem. Abstr. 2007, 148, 449523
- 17 Ebenbeck W, Rampf F, Marhold A. Pat. Appl US 20040229929, 2004 ; Chem. Abstr. 2004, 141, 106468.
- 18 Ralph JM, Faitg TH, Silva DJ, Feng Y, Blackledge CW, Adams JL. Tetrahedron Lett. 2009; 50: 1377
- 19 Clarke PA, Kayaleh NE, Smith MA, Baker JR, Bird SJ, Chan C. J. Org. Chem. 2002; 67: 5226