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
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 09. November 2015

Accepted after revision: 12. Dezember 2015

Publikationsdatum:
05. Januar 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

 
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  • 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.