Synlett 2016; 27(07): 1110-1115
DOI: 10.1055/s-0035-1561202
letter
© Georg Thieme Verlag Stuttgart · New York

FeBr3-Catalyzed Tandem Reaction of N-Propargylamides with Disulfides or Diselenides for the Synthesis of Oxazole Derivatives

Xu-Hong Gao
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: dcl78@wzu.edu.cn
,
Peng-Cheng Qian
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: dcl78@wzu.edu.cn
,
Xing-Guo Zhang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: dcl78@wzu.edu.cn
,
Chen-Liang Deng*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: dcl78@wzu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 09 November 2015

Accepted after revision: 12 December 2015

Publication Date:
05 January 2016 (online)


Abstract

A methodology of FeBr3-catalyzed tandem reaction of N-propargylamides with disulfides or diselenides for the formation of oxazole derivatives has been developed. The strategy includes several steps in one pot. Series of N-propargylamides and disulfides were suitable as substrates in this transformation for synthesizing the corresponding oxazole derivatives in moderate to good yields.

Supporting Information

 
  • References

  • 1 Alonso F, Beletskaya IP, Yus M. Chem. Rev. 2004; 104: 3079
    • 2a Lindquist N, Fenical W. J. Am. Chem. Soc. 1991; 113: 2303
    • 2b Garfunkle J, Ezzili C, Rayl TJ, Hochstatter DG, Hwang I, Boger DL. J. Med. Chem. 2008; 51: 4392
    • 3a Zheng M, Huang L, Huang H, Li X, Wu W, Jiang H. Org. Lett. 2014; 16: 5906
    • 3b Yu J, Yang H, Fu H. Adv. Synth. Catal. 2014; 356: 3669
    • 3c Yu X, Xin X, Wan B, Li X. J. Org. Chem. 2013; 78: 4895
    • 3d Hu Y, Yi R, Wang C, Xin X, Wu F, Wan B. J. Org. Chem. 2014; 79: 3052
    • 3e Bartoli G, Cimarelli C, Cipolletti R, Diomedi S, Giovannini R, Mari M, Marsili L, Marcantoni E. Eur. J. Org. Chem. 2012; 630
    • 3f Kreisberg JD, Magnus P, Shinde S. Tetrahedron Lett. 2002; 43: 7393
    • 4a Weyrauch JP, Hashmi AS. K, Schuster A, Hengst T, Schetter S, Littmann A, Rudolph M, Hamzic M, Visus J, Rominger F, Frey W, Bats JW. Chem. Eur. J. 2010; 16: 956
    • 4b Hashmi AS. K, Weyrauch JP, Frey W, Bats JW. Org. Lett. 2004; 6: 4391
    • 4c Egorova OA, Seo H, Kim Y, Moon D, Rhee YM, Ahn KH. Angew. Chem. Int. Ed. 2011; 50: 11446
    • 5a Arcadi A, Cacchi S, Cascia L, Fabrizi G, Marinelli F. Org. Lett. 2001; 3: 2501
    • 5b Beccalli EM, Borsini E, Broggini G, Palmisano G, Sottocornola S. J. Org. Chem. 2008; 73: 4746
    • 5c Merkul E, Müller TJ. J. Chem. Commun. 2006; 4817
  • 6 Kreisberg JD, Magnus P, Shinde S. Tetrahedron Lett. 2002; 43: 7393
    • 7a Senadi GC, Hu W.-P, Hsiao JS, Vandavasi JK, Chen C.-Y, Wang J.-J. Org. Lett. 2012; 14: 4478
    • 7b Malosh CF, Ready JM. J. Am. Chem. Soc. 2004; 126: 10240
    • 7c Patil NT, Singh V. Chem. Commun. 2011; 47: 11116
    • 8a Meng X, Kim S. Org. Biomol. Chem. 2011; 9: 4429
    • 8b Onizawa Y, Kusama H, Iwasawa N. J. Am. Chem. Soc. 2008; 130: 802
    • 8c Kusama H, Yamabe H, Onizawa Y, Hoshino T, Iwasawa N. Angew. Chem. Int. Ed. 2005; 44: 468
  • 9 Milton MD, Inada Y, Nishibayashi Y, Uemura S. Chem. Commun. 2004; 2712
    • 10a Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2008; 37: 1108
    • 10b Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 2617
    • 11a Du HA, Tang RY, Deng CL, Liu Y, Li JH, Zhang XG. Adv. Synth. Catal. 2011; 353: 2739
    • 11b Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
    • 11c Correa A, Elmore S, Bolm C. Chem. Eur. J. 2008; 14: 3527
  • 12 Typical Procedure Under air atmosphere, a reaction tube was charged with N-(prop-2-yn-1-yl)benzamide (1a, 0.2 mmol), diphenyldisulfane (2a, 0.4 mmol), FeBr3 (10 mol%), I2 (0.8 mmol), and MeCN (2 mL). The vessel was sealed and heated at 100 °C (oil bath temperature) for 12 h and then cooled to room temperature. The reaction mixture was washed with sat. Na2S2O3 (2 × 15 mL) and then brine (1 × 15 mL). After the aqueous layer was extracted with EtOAc, the combined organic layers were dried over anhydrous Na2SO4, and evaporated under vacuum. The residue was purified by flash column chromatography (hexane–EtOAc) to afford the desired product 3a. 2-Phenyl-5-[(phenylthio)methyl]oxazole (3a) Yellow solid (40.1 mg, 75% yield); mp 43–44 °C. 1H NMR (500 MHz, CDCl3): δ = 7.87 (dd, J = 5.9, 2.3 Hz, 2 H), 7.33–7.32 (m, 3 H), 7.30–7.28 (m, 2 H), 7.21–7.18 (m, 2 H), 7.16–7.13 (m, 1 H), 6.76 (s, 1 H), 4.03 (s, 2 H). 13C NMR (125 MHz, CDCl3): δ = 161.5, 148.4, 134.5, 131.3, 130.2, 129.0, 128.6, 127.3, 127.3, 126.1, 125.9, 29.7. LRMS (EI, 70 eV): m/z (%) = 267 (5) [M+], 158 (100), 130 (15), 104 (14), 77 (8). ESI-HRMS: m/z calcd for C16H14NOS+ [M + H]+: 268.0791; found: 286.0794.