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-00000083.xml
Synlett 2016; 27(09): 1397-1402
DOI: 10.1055/s-0035-1561566
DOI: 10.1055/s-0035-1561566
letter
Synthesis of Novel Imidazopyrrolo-Fused Isoxazole Derivatives through Acid-Mediated Intramolecular 1,3-Dipolar Cycloaddition
Further Information
Publication History
Received: 24 November 2015
Accepted after revision: 15 January 2016
Publication Date:
04 March 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201609/lookinside/thumbnails/st-2015-w0913-l_10-1055_s-0035-1561566-1.jpg)
Abstract
A facile approach to 4H-imidazo[1′,2′:1,2]pyrrolo[3,4-c]isoxazole derivatives was developed via intramolecular 1,3-dipolar cycloaddition catalyzed by p-toluenesulfonic acid. The method allows the convenient construction of novel tricyclic isoxazoles under mild reaction conditions and moderate yields.
Key words
1,3-dipolar cycloaddition - 2-nitro-1,1-ethenediamine - nitromethylene-imidazolidine - p-toluenesulfonic acid - tricyclic isoxazolesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561566.
- Supporting Information
-
References
- 1a Giovannoni MP, Vergelli C, Ghelardini C, Galeotti N, Bartolini A, Dal Piaz V. J. Med. Chem. 2003; 46: 1055
- 1b Li WT, Hwang DR, Chen CP, Shen CW, Huang CL, Chen TW, Lin CH, Chang YL, Chang YY, Lo YK, Tseng HY, Lin CC, Song JS, Chen HC, Chen SJ, Wu SH, Chen CT. J. Med. Chem. 2003; 46: 1706
- 1c Filer CN, Lacy JM, Peng CT. Synth. Commun. 2005; 35: 967
- 1d Lee YG, Koyama Y, Yonekawa M, Takata T. Macromolecules 2009; 42: 7709
- 1e Heasley B. Angew. Chem. Int. Ed. 2011; 50: 8474
- 2 Conti P, Dallanoce C, Amici MD, Micheli CD, Klotz KN. Bioorg. Med. Chem. 1998; 6: 401
- 3 Mishra A, Jain SK, Asthana JG. Orient. J. Chem. 1998; 14: 151
- 4 Kang YY, Shin KJ, Yoo KH, Seo KJ, Hong CY, Lee CS, Park SY, Kim DJ, Park SW. Bioorg. Med. Chem. Lett. 2000; 10: 95
- 5 You Z, Lee J. Med. Chem. Res. 1998; 8: 313
- 6 Sechi M, Sannia L, Carta F, Palomba M, Dallocchio R, Dessi A, Derudas M, Zawahir Z, Neamati N. Antiviral Chem. Chemother. 2005; 16: 41
- 7a Simoni D, Grisolia G, Giannini G, Roberti M, Rondanin R, Piccagli L, Baruchello R, Rossi M, Romagnoli R, Invidiata FP, Grimaudo S, Jung MK, Hamel E, Gebbia N, Crosta L, Abbadessa V, Di Cristina A, Dusonchet L, Meli M, Tolomeo M. J. Med. Chem. 2005; 48: 723
- 7b Kaffy J, Pontikis R, Carrez D, Croisy A, Monneret C, Florent JC. Bioorg. Med. Chem. 2006; 14: 4067
- 8a Brown DH, Styring P. Liq. Cryst. 2003; 30: 23
- 8b Iglesias R, Serrano JL, Sierra T. Liq. Cryst. 1997; 22: 37
- 8c Gallardo H, Zucco C, Da Silva L. Mol. Cryst. Liq. Cryst. 2002; 373: 181
- 8d Bartulin J, Martinez R, Gallardo H, Muller J, Taylor TR. Mol. Cryst. Liq. Cryst. 1993; 225: 175
- 8e Seguel CG, Borchers B, Haase W, Aguilera C. Liq. Cryst. 1992; 11: 899
- 8f Sham MS, Shubhi J, Monica D, Ashok K. Med. Chem. 2008; 4: 146
- 9 Subash V, Michael B, Reaz U, Baojie W, Scott GF, Pavel AP. J. Med. Chem. 2008; 51: 1999
- 10 Kim HJ, Lee JH, Olmstead MM, Kurth MJ. J. Org. Chem. 1992; 57: 6513
- 12 Santos MM. M, Faria N, IIey J, Coles SJ, Hursthouse MB, Martins ML, Moreira R. Bioorg. Med. Chem. Lett. 2010; 20: 193
- 13 Andres JI, Alcázar J, Alonso JM, Alvarez RM, Bakker MH, Biesmans I, Cid JM, Lucas AI. D, Fernández J, Font LM, Hens KA, Iturrino L, Lenaerts I, Martínez S, Megens AA, Pastor J, Vermote PC. M, Steckler T. J. Med. Chem. 2005; 48: 2054
- 14 Andres JH, Alcazar J, Alonso JM, Lucas AI. D, Iturrino L, Biesmans I, Megens AA. Bioorg. Med. Chem. 2006; 14: 4361
- 15 Soro Y, Bamba F, Siaka S, Coustard JM. Tetrahedron Lett. 2006; 47: 3315
- 16a Larsen KE, Torssell KB. G. Tetrahedron 1984; 40: 2985
- 16b Tang S, He J, Sun Y, He L, She X. Org. Lett. 2009; 11: 3982
- 16c Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
- 16d Waldo JP, Larock RC. Org. Lett. 2007; 9: 643
- 16e Dadiboyena S, Xu J, Hamme AT. II. Tetrahedron Lett. 2007; 48: 1295
- 17 CCDC 1437621 (5k) and 1437622 (6k) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 18 Kürti L, Czakó B. Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Academic Press; Burlington: 2005: 7
- 19 Zhao YL, Di CH, Liu SD, Meng J, Liu Q. Adv. Synth. Catal. 2012; 354: 3545
- 20 Typical Procedure for 6-Benzyl-3-phenyl-4H-imidazo-[1′,2′:1,2]pyrrolo[3,4-c]isoxazole (5a)The mixture of 4a (0.2 mmol) and TsOH (0.2 mmol) in MeOH–H2O (1:1; 8 mL) was heated to 80 °C and stirred overnight. The reaction was monitored by TLC. After completion, the mixture was evaporated under reduced pressure and extracted with CH2Cl2 (3 × 20 mL). The organic phase was combined, evaporated under reduced pressure, then purified by column chromatography (CH2Cl2–EtOAc, 10:1) to afford 5a; yield 68%; white solid; mp 209.7–210.6 °C. 1H NMR (400 MHz, CDCl3): δ = 7.63–7.59 (dd, J = 8.0, 2.0 Hz, 2 H), 7.49–7.46 (m, 3 H), 7.39–7.33 (m, 2 H), 7.30 (d, J = 7.2 Hz, 1 H), 7.27–7.23 (m, 2 H), 7.20 (s, 1 H), 7.04 (s, 1 H), 4.62 (s, 2 H), 4.08 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 160.7, 159.3, 141.3, 136.5, 133.3, 130.8, 130.6, 129.3, 129.0, 128.5, 127.2, 126.4, 126.2, 117.5, 42.4, 30.9. ESI-HRMS: m/z calcd for C20H16N3O [M + H]+: 314.1293; found: 314.1292.