A Convenient One-Pot Synthesis of N-Substituted 2-Aminoazole Derivatives

Sirilata Yotphan; Danupat Beukeaw; Vichai Reutrakul

doi:10.1055/s-0032-1316868

Synthesis, Table of Contents

Synthesis 2013; 45(7): 936-942
DOI: 10.1055/s-0032-1316868

paper

A Convenient One-Pot Synthesis of N-Substituted 2-Aminoazole Derivatives

Sirilata Yotphan*

Center for Catalysis and Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand Fax: +66(2)3547151 Email: sirilata.yot@mahidol.ac.th

,

Danupat Beukeaw

Center for Catalysis and Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand Fax: +66(2)3547151 Email: sirilata.yot@mahidol.ac.th

,

Vichai Reutrakul

Center for Catalysis and Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand Fax: +66(2)3547151 Email: sirilata.yot@mahidol.ac.th

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Abstract

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Abstract

A practical protocol for the one-pot synthesis of N-substituted 2-aminoazole derivatives is described, employing simple azole substrates, nitrogen nucleophiles, lithium tert-butoxide as the base, and iodine to mediate carbon–nitrogen bond formation. This method proceeds at room temperature under an air atmosphere using a normal benchtop set-up, or can be performed conveniently using microwave irradiation.

Key words

N-substituted 2-aminoazoles - iodine - one-pot synthesis - benzoxazole - carbon–nitrogen bond formation

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References

References

Selected literature:

1a Martins MA. P, Frizzo CP, Moreira DN, Buriol L, Machado P. Chem. Rev. 2009; 109: 4140
1b Veh VS. C, Iyengar R. In Comprehensive Heterocyclic Chemistry III . Vol. 4. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Pergamon; Oxford: 2008: 487-542
1c Sheng C, Xu H, Wang W, Cao Y, Dong G, Wang S, Che X, Ji H, Miao Z, Yao J, Zhang W. Eur. J. Med. Chem. 2010; 45: 3531

Selected references on natural products or biologically active molecules that contain substituted 1,3-azoles. Imidazoles:

2a Gordon T, Hansen P, Morgan B, Singh J, Baizman E, Ward S. Bioorg. Med. Chem. Lett. 1993; 3: 915
2b von Geldern TW, Kester JA, Bal R, Wu-Wong JR, Chiou W, Dixon DB, Opgenorth TJ. J. Med. Chem. 1996; 39: 968
2c Pridgen LN, Mokhallalati MK, McGuire MA. Tetrahedron Lett. 1997; 38: 1275

Thiazoles:

2d Bagley MC, Bashford KE, Hesketh CL, Moody CJ. J. Am. Chem. Soc. 2000; 122: 3301
2e Wipf P, Venkatraman S. J. Org. Chem. 1995; 60: 1224
2f Cetusic JR. P, Green FR, Graupner PR, Oliver MP. Org. Lett. 2002; 4: 1307

Oxazoles:

2g Kreisberg JD, Magnus P, McIver EG. Tetrahedron Lett. 2001; 42: 627
2h Nogle LM, Marquez BL, Gerwick WH. Org. Lett. 2003; 5: 3
2i Evans DA, Cee VJ, Smith TE, Santiago KJ. Org. Lett. 1999; 1: 87

3a Liu KG, Lo JR, Comery TA, Zhang GM, Zhang JY, Kowal DM, Smith DL, Kerns EH, Schechter LE, Robichaud AJ. Bioorg. Med. Chem. Lett. 2009; 19: 1115
3b O’Donnell CJ, Rogers BN, Bronk BS, Bryce DK, Coe JW, Cook KK, Duplantier AJ, Evrard E, Hajos M, Hoffmann WE, Hurst RS, Maklad N, Mather RJ, McLean S, Nedza FM, O’Neill BT, Peng L, Qian W, Rottas MM, Sands SB, Schmidt AW, Shrikhande AV, Spracklin DK, Wong DF, Zhang A, Zhang L. J. Med. Chem. 2010; 53: 1222

4a Whitman DB, Cox CD, Breslin MJ, Brashear KM, Schreier JD, Bogusky MJ, Bednar RA, Lemaire W, Bruno JG, Hartman GD, Reiss DR, Harrell CM, Kraus RL, Li Y, Garson SL, Doran SC, Prueksaritanont T, Li C, Winrow CJ, Koblan KS, Renger JJ, Coleman PJ. ChemMedChem. 2009; 4: 1069
4b Cox CD, Breslin MJ, Whitman DB, Schreier JD, McGaughey GB, Bogusky MJ, Roecker AJ, Mercer SP, Bednar RA, Lemaire W, Bruno JG, Reiss DR, Harrell CM, Murphy KL, Garson SL, Doran SM, Prueksaritanont T, Anderson WB, Tang C, Roller S, Cabalu TD, Cui D, Hartman GD, Young SD, Koblan KS, Winrow CJ, Renger JJ, Coleman PJ. J. Med. Chem. 2010; 53: 5320

5a Armstrong A, Collins JC. Angew. Chem. Int. Ed. 2010; 49: 2282
5b Denny WA. Anti-Cancer Drug Des. 1989; 4: 241
5c Herzig SJ, Howell MD, Ngo LH, Marcantonio ER. J. Am. Med. Assoc. 2009; 301: 2120

6a Dodson RM, King LC. J. Am. Chem. Soc. 1944; 67: 2242
6b King LC, Hlavacek RJ. J. Am. Chem. Soc. 1950; 72: 3722

7 For a recent report, see: Liu KG, Lo JR, Comery TA, Zhang GM, Zhang JY, Kowal DM, Smith DL, Di L, Kerns EH, Schechter LE, Robichaud AJ. Bioorg. Med. Chem. Lett. 2009; 19: 1115

8a Wolfe JP, Wagaw S, Marcoux J.-F, Buchwald SL. Acc. Chem. Res. 1998; 31: 805
8b Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
8c Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400 ; Angew. Chem. 2003, 115, 5558

9a Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
9b Monguchi D, Fujiwara T, Furukawa H, Mori A. Org. Lett. 2009; 11: 1607
9c Wang Q, Schreiber SL. Org. Lett. 2009; 11: 5178

10a Froehr T, Sindlinger CP, Kloeckner U, Finkbeiner P, Nachtsheim BJ. Org. Lett. 2011; 13: 3754
10b Iamani M, Prabhu KR. J. Org. Chem. 2011; 76: 7938
10c Wagh YS, Sawant DN, Bhanage BM. Tetrahedron Lett. 2012; 53: 3482
10d Wertz S, Shintaro K, Studer A. Angew. Chem. Int. Ed. 2011; 50: 11511
10e Guo S, Qian B, Xie Y, Xia C, Huang H. Org. Lett. 2011; 13: 522

11a Do H.-Q, Daugulis O. Org. Lett. 2009; 11: 421
11b Popov I, Do H.-Q, Daugulis O. J. Org. Chem. 2009; 74: 8309

12 See the Supporting Information for additional details.
13 Taft RW, Bordwell FG. Acc. Chem. Res. 1988; 21: 463
14 Cioffi CL, Lansing JJ, Yuksel H. J. Org. Chem. 2010; 75: 7942

15a Ma D, Lu X, Shi L, Zhang H, Jiang Y, Liu X. Angew. Chem. Int. Ed. 2011; 50: 1118
15b Khalaf AI, Alvarez RG, Sucking CJ, Waigh RD. Tetrahedron 2000; 56: 8567

16 Hooper MW, Utsunomiya M, Hartwig JF. J. Org. Chem. 2003; 68: 2861
17 Blicke FF, Godt HC. Jr. J. Am. Chem. Soc. 1954; 76: 2835

Supplementary Material

Supporting Information