Synlett, Table of Contents Synlett 2016; 27(07): 1110-1115DOI: 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 Recommend Article Abstract Buy Article All articles of this category 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. Key words Key wordsFeBr3 - tandem - N-propargylamides - disulfides - oxazole Full Text References 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. Supplementary Material Supplementary Material Supporting Information
