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Synthesis 2014; 46(11): 1487-1492
DOI: 10.1055/s-0033-1340983
DOI: 10.1055/s-0033-1340983
paper
Synthesis and Functionalization of 3-Azolylquinoxalin-2(1H)-ones
Further Information
Publication History
Accepted after revision: 21 February 2014
Received: 23 December 2013
Publication Date:
03 April 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201411/lookinside/thumbnails/10.1055-s-0033-1340983-1.jpg)
Abstract
Ethyl 2-azolylglyoxylates react smoothly with o-phenylenediamines and 1,2-diaminocyclohexane in acetonitrile at room temperature to give the corresponding 3-azolylquinoxalin-2(1H)-ones and their saturated analogues in good to excellent yields.
Key words
quinoxalin-2(1H)-ones - 2-azolylglyoxylates - condensation - o-phenylenediamine - 1,2-diaminocyclohexaneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Carta A, Piras S, Loriga G, Paglietti G. Mini-Rev. Med. Chem. 2006; 6: 1179 ; and references therein
- 2 Nikam SS, Bigge CF. Drugs Future 1999; 24: 1107
- 3 Hyae-Gyeong C, Chul-Min L, Beom-Tae K, Ki-jun H. Bioorg. Med. Chem. Lett. 2004; 14: 2661
- 4 Xun L, Yonggang L, Wenfang X, Jian Z, Huawei Z. Bioorg. Med. Chem. 2010; 18: 1516
- 5 El-Sabbagh OI, El-Sadek ME, Lashine SM, Yassin SH, El-Nabtity SM. Med. Chem. Res. 2009; 18: 782
- 6 Patel M, Mchugh RJ, Cordova BC, Klabe RM, Erickson-Viitanen S, Trainor GL, Rodgers JD. Bioorg. Med. Chem. Lett. 2000; 10: 1729
- 7 Willardsen JA, Dudley DA, Cody WL, Chi L, McClanahan TB, Mertz TE, Potoczak RE, Narasimhan LS, Holland DR, Rapundalo ST, Edmunds JJ. J. Med. Chem. 2004; 47: 4089
- 8 Carta A, Sanna P, Loriga M, Setzu MG, La Colla P, Loddo R. Farmaco 2002; 57: 19
- 9 Tang AH, Franklin SR, Himes CS, Ho PM. J. Pharmacol. Exp. Ther. 1991; 259: 248
- 10 Ager IR, Barnes AC, Danswan GW, Hairsine PW, Kay DP, Kennewell PD, Matharu SS, Miller P, Robson P, Rowlands DA, Tully WR, Westwood R. J. Med. Chem. 1988; 31: 1098
- 11 Manca P, Peana A, Savelli F, Mule A, Pirisino G. Farmaco 1992; 47: 519
- 12 Brown DJ In Quinoxalines: Supplement II . Taylor EC, Wipf P, Weissberger A. John Wiley & Sons; New Jersey: 2004. 92. 1-189-239
- 13 Gris J, Glisoni R, Fabian L, Fernández B, Moglioni A. Tetrahedron Lett. 2008; 49: 1053
- 14 Andrioletti B, Rose E, Szydlo F, Duhayon C. Tetrahedron Lett. 2008; 49: 3749
- 15 Mukherjee C, Watanabe K, Biehl E. Tetrahedron Lett. 2012; 53: 6008
- 16 Shi F, Tan W, Zhang H, Li M, Ye Q, Ma G, Tu S, Li G. Adv. Synth. Catal. 2013; 355: 3715
- 17 Geraschenko OV, Khodakovskiy P, Shishkin O, Mykhailiuk P, Zaporozhets O, Tolmachev A. Synthesis 2011; 1633
- 18 Geraschenko OV, Khodakovskiy PV, Shivanyuk ON, Shishkin OV, Mykhailiuk PK, Tolmachev AA. Synthesis 2012; 44: 1263
- 19 Soloshonok VA, Ono T. J. Org. Chem. 1997; 62: 3030
- 20 Unfortunately, all attempts to isolate the cis isomers from the mother liquor failed.
- 21 CCDC number for compound 6c is 913386.