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Synthesis 2012; 44(13): 2070-2078
DOI: 10.1055/s-0031-1291160
DOI: 10.1055/s-0031-1291160
paper
Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles
Further Information
Publication History
Received: 20 February 2012
Accepted after revision: 23 April 2012
Publication Date:
14 June 2012 (online)
Abstract
A range of 4- and 5-substituted N-benzyl-1,2,3-triazoles have been submitted to debenzylation using Pd/C and hydrogen in the presence of 1,1,2-trichloroethane. Triazoles with oxygen-containing substituents are efficiently debenzylated under these conditions. Triazoles with a phenyl or benzyl substituent on C4 or C5 are not debenzylated, whereas a pentyl-substituted derivative was readily debenzylated.
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References
- 1a Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 1b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 2 Krasiński A, Fokin VV, Sharpless KB. Org. Lett. 2004; 6: 1237
- 3 Zhang L, Chen X, Xue P, Sun HH. Y, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
- 4a Dabak K, Sezer Ö, Akar A, Anaç O. Eur. J. Med. Chem. 2003; 38: 215
- 4b Baures PW. Org. Lett. 1999; 1: 249
- 4c Komeda S, Lutz M, Spek AL, Yamanaka Y, Sato T, Chikuma M, Reedijk J. J. Am. Chem. Soc. 2002; 124: 4738
- 4d Fan W In Comprehensive Heterocyclic Chemistry II . Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996. 1-126
- 5 Lu L.-H, Wu J.-H, Yang C.-H. J. Chin. Chem. Soc (Taipei, Taiwan) 2008; 55: 414
- 6 Jin T, Kamijo S, Yamamoto Y. Eur. J. Org. Chem. 2004; 3789
- 7a Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L. J. Org. Chem. 2005; 70: 6526
- 7b Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F. Angew. Chem. Int. Ed. 2006; 45: 6893
- 7c Zhang W, Kuang C, Yang Q. Synthesis 2010; 283
- 8a Kamijo S, Jin T, Huo Z, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 7786
- 8b Looker JJ. J. Org. Chem. 1965; 30: 638
- 8c Loren JC, Krasiński A, Fokin VV, Sharpless KB. Synlett 2005; 2847
- 9 Wiley RH, Hussung KF, Moffat J. J. Org. Chem. 1956; 21: 190
- 10 Buckle DR, Rockell CJ. M, Oliver RS. J. Heterocycl. Chem. 1982; 19: 1147
- 11a Boechat N, Ferreira Mde L. G, Bastos MM, Camilo AL. S, Wardell SM. S. V, Wardell JL, Tiekink ER. T. J. Chem. Crystallogr. 2010; 40: 1137
- 11b Pati HN, Wicks M, Holt HL. Jr, LeBlanc R, Weisbruch P, Forrest L, Lee M. Heterocycl. Commun. 2005; 11: 117
- 11c Youcef RA, Dos Santos M, Roussel S, Baltaze J.-P, Lubin-Germain N, Uziel J. J. Org. Chem. 2009; 74: 4318
- 12 Farooq T, Sydnes LK, Törnroos KW, Haug BE. Monatsh. Chem. 2012; 143: 505
- 13 Evans GB, Furneaux RH, Greatrex B, Murkin AS, Schramm VL, Tyler PC. J. Med. Chem. 2008; 51: 948
- 14 Cheng C, Sun J, Xing L, Xu J, Wang X, Hu Y. J. Org. Chem. 2009; 74: 5671
- 15 Sydnes LK, Holmelid B, Sengee M, Hanstein M. J. Org. Chem. 2009; 74: 3430
- 16 Abboud J.-LM, Foces-Foces C, Notario R, Trifonov RE, Volovodenko AP, Ostrovskii VA, Alkorta I, Elguero J. Eur. J. Org. Chem. 2001; 3013
- 17 CCDC860712 contains the supplementary crystallographic data for 2g. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
- 18 Dabbagh HA, Rasti E, Najafi ChermahiniA. THEOCHEM 2010; 947: 92
- 19 Ozimiński WP, Dobrowolski JC, Mazurek AP. J. Mol. Struct. 2003; 651-653: 697-704
- 20 CCDC 860711 contains the supplementary crystallographic data for 2m. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
- 21 Kalisiak J, Sharpless KB, Fokin VV. Org. Lett. 2008; 10: 3171
- 22 Nakamura T, Terashima T, Ogata K, Fukuzawa S.-i. Org. Lett. 2011; 13: 620
- 23 Raghavendra MS, Lam Y. Tetrahedron Lett. 2004; 45: 6129
- 24 Leeb L, Gmeiner P, Löber S. QSAR Comb. Sci. 2007; 26: 1145
- 25 Asano K, Matsubara S. Org. Lett. 2010; 12: 4988
- 26 Jlalia I, Beauvineau C, Beauvière S, Önen E, Aufort M, Beauvineau A, Khaba E, Herscovici J, Meganem F, Girard C. Molecules 2010; 15: 3087
- 27 Martina K, Leonhardt SE. S, Ondruschka B, Curini M, Binello A, Cravotto G. J. Mol. Catal. A: Chem. 2011; 334: 60
- 28 Jin T, Yan M, Menggenbateer Minato T, Bao M, Yamamoto Y. Adv. Synth. Catal. 2011; 353: 3095
- 29 Margetic D, Butler DN, Warrener RN. Aust. J. Chem. 2000; 53: 959
- 30 Yap AH, Weinreb SM. Tetrahedron Lett. 2006; 47: 3035
- 31 Cohrt AE, Jensen JF, Nielsen TE. Org. Lett. 2010; 12: 5414