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 2014; 46(18): 2451-2462
DOI: 10.1055/s-0033-1339139
DOI: 10.1055/s-0033-1339139
paper
Oxazole/Thiazole and Triazole Hybrids Based on α-Amino Acids
Further Information
Publication History
Received: 30 January 2014
Accepted after revision: 29 April 2014
Publication Date:
04 June 2014 (online)
Abstract
The Cu(I)-catalyzed Huisgen [3+2] cycloaddition is the basis of click chemistry to synthesize triazole derivatives by coupling azides with ethynyl blocks. In the development of new compounds inspired by bioactive natural products, the synthesis of new oxazole building blocks containing azide moiety and coupling them with aromatic alkynes via triazole linker is described. These oxazole building blocks are synthesized using amino acids as chiral and inexpensive starting materials. Using this approach, 16 new triazole-oxazole hybrids were synthesized.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Miranda PO, Díaz DD, Padrón JI, Bermejo J, Martín VS. Org. Lett. 2003; 11: 1979
- 1b Carballo RM, Ramírez MA, Rodríguez ML, Martín VS, Padrón JI. Org. Lett. 2006; 8: 3837
- 1c Miranda PO, Padrón JM, Padrón JI, Villar J, Martín VS. ChemMedChem 2006; 1: 323
- 1d Purino MA, Ramírez MA, Daranas AH, Martín VS, Padrón JI. Org. Lett. 2012; 14: 5904
- 1e Rutkowski J, Brzezinski B. Biomed. Res. Int. 2013; 2013: 162513
- 2a García C, Soler MA, Martín VS. Tetrahedron Lett. 2000; 41: 4127
- 2b Crisóstomo FR. P, Carrillo R, León LG, Martín T, Padrón JM, Martín VS. J. Org. Chem. 2006; 71: 2339
- 2c Díaz DD, Betancort JM, Martín VS. Synlett 2007; 343
- 2d Rodríguez-López J, Crisóstomo FP, Ortega N, López-Rodríguez M, Martín VS, Martín T. Angew. Chem. Int. Ed. 2013; 52: 3659
- 2e Martín T, Martín VS, Padrón JI. Synlett 2014; 25: 12
- 3 McNally A, Prier CK, MacMillan DW. Science 2011; 334: 1114
- 4a Jin Z. Nat. Prod. Rep. 2013; 30: 869
- 4b Davyt D, Serra G. Mar. Drugs 2010; 8: 2755
- 4c Yeh VS. C. Tetrahedron 2004; 60: 11995
- 5a Gant TG, Meyers AI. Tetrahedron 1994; 50: 2927
- 5b Meyers AI, Tavares F. Tetrahedron Lett. 1994; 35: 2481
- 6 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
- 7 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 8 Yoon J, Ryu JS. Bioorg. Med. Chem. Lett. 2010; 20: 3930
- 9a Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
- 9b Chrysina ED, Bokor É, Alexacou K-M, Charavgi M-D, Oikonomakos GN, Zographos SE, Leonidas DD, Oikonomakos NG, Somsák L. Tetrahedron: Asymmetry 2009; 20: 733
- 9c Colombo F, Tintori C, Furlan A, Borrelli S, Christodoulou MS, Dono R, Maina F, Botta M, Amat M, Bosch J, Passarella D. Bioorg. Med. Chem. Lett. 2012; 22: 4693
- 10a Metha G, Singh V. Chem. Soc. Rev. 2002; 31: 324
- 10b Tietze LF, Bell HP, Chandrasekhar S. Angew. Chem. Int. Ed. 2003; 42: 3996
- 11a Mann E, Chana A, Sánchez-Sancho F, Puerta C, García-Merino A, Herradón B. Adv. Synth. Catal. 2002; 344: 855
- 11b Steiner AJ, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM. Carbohydr. Res. 2007; 342: 1850
- 11c Banerjee A, Sergienko E, Vasile S, Gupta V, Vuori K, Wipf P. Org. Lett. 2009; 11: 65
- 11d Burov S, Leko M, Dorosh M, Dobrodumov A, Veselkina O. J. Pept. Sci. 2011; 17: 620
- 12 Hou J, Li Z, Fang Q, Feng C, Zhang H, Guo W, Wang H, Gu G, Tian Y, Liu P, Liu R, Lin J, Shi Y, Yin Z, Shen J, Wang PG. J. Med. Chem. 2012; 55: 3066
- 13 Li W, Chou H. Synthesis 2000; 84
- 14 Phillips AJ, Uto Y, Wipf P, Reno MJ, Williams DR. Org. Lett. 2000; 2: 1165
- 15a Goddard-Borger ED, Stick RV. Org. Lett. 2007; 9: 3797
- 15b Nyffeler PT, Liang C-H, Koeller KM, Wong C-H. J. Am. Chem. Soc. 2002; 124: 10773
- 16 Wipf P, Miller CP, Venkatraman S, Fritch PC. Tetrahedron Lett. 1995; 36: 6395
- 17 Fuchs PL, Corey EJ. Tetrahedron Lett. 1972; 13: 3769
- 18 He R, Chen Y, Chen Y, Ougolkov AV, Zhang J, Savoy DN, Billadeau DD, Kozikowski AP. J. Med. Chem. 2010; 53: 1347
- 19 Chattopadhyay SK, Pal BK, Biswas S. Synth. Commun. 2005; 35: 1167
- 20 Ferreira PM, Monteiro LS, Pereira G, Ribeiro L, Sacramento J, Silva S. Eur. J. Org. Chem. 2007; 5934
- 21 Sellanes D, Campot F, Núñez I, Lin G, Espósito P, Dematteis S, Saldaña J, Domínguez L, Manta E, Serra G. Tetrahedron 2010; 66: 5384
- 22 Huh DH, Jeong JS, Lee HB, Ryu H, Kim YG. Tetrahedron 2002; 58: 9925
- 23 Kundu NG, Khan MW. Tetrahedron 2000; 56: 4777
- 24 Gupton JT, Telang N, Banner EJ, Kluball EJ, Hall KE, Finzel KL, Jia X, Bates SR, Welden RS, Giglio BC, Eaton JE, Barelli PJ, Firich LT, Stafford JA, Coppock MB, Worrall EF, Kanters RP. F, Keertikar K, Osterman R. Tetrahedron 2010; 66: 9113
- 25 Shimada N, Hanari T, Kurosaki Y, Anada M, Nambu H, Shiro M, Hashimoto S. J. Org. Chem. 2010; 75: 6039
- 26 Schmittel M, Morbach G, Schenk WA, Hagel M. J. Chem. Crystallogr. 2005; 35: 373