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Synthesis 2013; 45(17): 2431-2437
DOI: 10.1055/s-0033-1339376
DOI: 10.1055/s-0033-1339376
paper
Efficient Multicomponent Synthesis of Mono-, Bis-, and Tris-1,2,3-triazoles Supported by Hydroxybenzene Scaffolds
Further Information
Publication History
Received: 02 May 2013
Accepted after revision: 17 June 2013
Publication Date:
23 July 2013 (online)
Abstract
A versatile one-pot synthesis of a series of mono-, bis- and tris-1,2,3-triazoles supported by commercially available hydroxybenzene scaffolds has been developed employing click chemistry. The multicomponent copper(I)-catalyzed 1,3-dipolar cycloaddition of sodium azide, propargyl bromide, and a para-substituted benzyl derivative yields N-benzyl-functionalized triazoles featuring several electron-donating or electron-withdrawing groups. Despite the preparation of highly substituted molecules, reaction conditions that provides good yields involved room temperature, times that oscillate between 16 and 24 hours, and catalyst loads ranging from 5–10 mol%. The present methodology could be useful for the building up of multi-triazole libraries easily tunable with donor or attractor functional groups.
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References
- 1a Fan W.-Q, Katritzky AR In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996: 1-126
- 1b Denhe H In Houben–Weyl Methoden der Organischen Chemie . Vol. E8d. Shumman E. Thieme; Stuttgart: 1994: 305
- 2a Alvarez R, Velazquez S, San F, Aquaro S, De C, Perno CF, Karlsson A, Balzarini J, Camarasa M. J. Med. Chem. 1994; 37: 4185
- 2b Velazquez S, Alvarez R, Perez C, Gago F, De C, Balzarini J, Camarasa M. J. Antivir. Chem. Chemother. 1998; 9: 481
- 2c Whitting M, Tripp JC, Lin YC, Lindstrom W, Olson AJ, Elder JH, Sharpless KB, Fokin VV. J. Med. Chem. 2006; 49: 7697
- 3a Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Garber DR, Grega KC, Hester JB, Hutchinson DK, Morris J, Reischr RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH. J. Med. Chem. 2000; 43: 953
- 3b Demaray JA, Thuener JE, Dawson MN, Sucheck SJ. Bioorg. Med. Chem. Lett. 2008; 18: 4868
- 4a Vicentini CB, Brandolini B, Guarneri M, Giori P. Farmaco 1992; 47: 1021
- 4b Joan CF. T, Elizabeth H, Beatrice M, Daniel PB. Antimicrob. Agents Chemother. 1998; 42: 313
- 4c Gaur M, Goel M, Sridhar L, Ashok TD. S, Prabhakar S, Dureja P, Raghunathan P, Eswaran SV. Monatsh. Chem. 2012; 143: 283
- 5a Passannanti A, Diana P, Barraja P, Mingoia F, Lauria A, Cirrincione G. Heterocycles 1998; 48: 1229
- 5b Yu JL, Wu QP, Zhang QS, Liu YH, Li YZ, Zhou ZM. Bioorg. Med. Chem. Lett. 2010; 20: 240
- 6 Brockunier LL, Parmee ER, Ok HO, Candelore MR, Cascieri MA, Colwell LF, Deng L, Feeney WP, Forest MJ, Hom GJ, Maclntyre DE, Tota L, Wyvratt MJ, Fisher MH, Weber AE. Bioorg. Med. Chem. Lett. 2000; 10: 2111
- 7 Hou DR, Alam S, Kaun TC, Ramathan M, Lin TP, Hung MS. Bioorg. Med. Chem. Lett. 2009; 19: 1022
- 8a L’abbé G. Chem. Rev. 1969; 69: 345
- 8b Huisgen R In 1,3-Dipolar Cycloaddition Chemistry . Padwa A. Chap. 1, Wiley; New York: 1984: 1-176
- 8c Padwa A In Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon; Oxford: 1991
- 8d Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
- 9 Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV. J. Am. Chem. Soc. 2005; 127: 210
- 10a Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
- 10b Appukkutan P, Dehaen W, Fokin VV, Van der Eycken E. Org. Lett. 2004; 6: 4223
-
10c Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett. 2004; 6: 2853
- 10d Cravotto G, Fokin VV, Garella D, Binello A, Boffa L, Barge A. J. Comb. Chem. 2010; 12: 13
- 11 Wang Y, Ji K, Lan S, Zang L. Angew. Chem. Int. Ed. 2012; 51: 1915
- 12 Negron-Silva GE, Gonzalez-Olvera R, Angeles BeltranD, Maldonado-Carmona N, Espinoza-Vazquez A, Palomar-Pardave ME, Romero-Romo MA, Santillan-Baca R. Molecules 2013; 18: 4613
- 13 Thomas JR, Liu X, Hergenrother PJ. J. Am. Chem. Soc. 2005; 127: 12434
- 14a Angell Y, Burgess K. Angew. Chem. Int. Ed. 2007; 46: 3649
- 14b Aizpurua JM, Azcune I, Fratila RM, Balentova E, Sagartzazu-Aizpurua M, Miranda JI. Org. Lett. 2010; 12: 1584
- 14c Oladeinde OA, Hong SY, Holland RJ, Maciag AE, Keefer LK, Saavedra JE, Nandurdikar RS. Org. Lett. 2010; 12: 4256
- 14d Zheng Z.-J, Ye F, Zheng L.-S, Yang K.-F, Lai G.-Q, Xu L.-W. Chem. Eur. J. 2012; 18: 14094
- 15a Lombardo CM, Welsh SJ, Strauss SJ, Dale AG, Todd AK, Nanjunda R, Wilson WD, Neidle S. Bioorg. Med. Chem. Lett. 2012; 22: 5984
- 15b Elamari H, Meganem F, Herscovici J, Girard C. Tetrahedron Lett. 2011; 52: 658
- 15c Arora SB, Shafi S, Singh S, Ismail T, Kumar HM. S. Carbohydr. Res. 2008; 43: 139
- 16a Lal K, Kumar A, Pavan MS, Kaushik CP. Bioorg. Med. Chem. Lett. 2012; 22: 4353
- 16b Yuan Z, Kuang G.-C, Clark RJ, Zhu L. Org. Lett. 2012; 14: 2590
- 16c Kwon M, Jang Y, Yoon S, Yang D, Jeon HB. Tetrahedron Lett. 2012; 53: 1606
- 16d Hung HC, Cheng C.-W, Ho I.-T, Chung W.-C. Tetrahedron Lett. 2009; 50: 302
- 16e Skarpos H, Osipov SN, Vorob’eva DV, Odinets IL, Lork E, Röshenthaler G.-V. Org. Biomol. Chem. 2007; 5: 2361
- 17 Rajakumar P, Kalpana V, Ganesan S, Maruthamuthu P. Tetrahedron Lett. 2011; 52: 5812
- 18 Moses JE, Ritson DJ, Zhang F, Lombardo CM, Haider S, Oldham N, Neidle S. Org. Biomol. Chem. 2010; 8: 2926
- 19a Scheweinfurth D, Demeshko S, Kushniyarov MM, Dechert S, Gurram V, Buchmeiser MR, Meyer F, Sarkar B. Inorg. Chem. 2012; 51: 7592
- 19b Donnelly PS, Zanatta SD, Zammit SC, White JM, Williams SJ. Chem. Commun. 2008; 44: 2459
- 19c Cristiano R, Eccher J, Bechtold IH, Tironi CN, Viera AA, Molin F, Gallardo H. Langmuir 2012; 28: 11590
- 19d Wang D, Denux D, Ruiz J, Astruc D. Adv. Synth. Catal. 2013; 355: 129
- 19e Jin J, Wang W, Liu Y, Hou H, Fan Y. Chem. Commun. 2011; 47: 7461
For general reviews on the chemistry of 1,2,3-triazoles: