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Synlett 2017; 28(12): 1496-1500
DOI: 10.1055/s-0036-1588779
letter
© Georg Thieme Verlag Stuttgart · New York

Silver-Catalyzed Intramolecular C(5)–H Acyloxylation of 1,4-Di­substituted 1,2,3-Triazoles

Yaowen Liu
a   Faculty of Science, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: ybjiang@kmust.edu.cn
,
Wensheng Zhang
b   School of Science and Technology, Jiaozuo Teachers’ College, Jiaozuo 454001, P. R. of China
,
Kai Xie
a   Faculty of Science, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: ybjiang@kmust.edu.cn
,
Yubo Jiang*
a   Faculty of Science, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: ybjiang@kmust.edu.cn
› Author AffiliationsSupported by: National Natural Science Foundation of China (21662020)
Further Information

Publication History

Received: 22 February 2017

Accepted after revision: 19 March 2017

Publication Date:
11 April 2017 (online)

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Abstract

Silver-catalyzed direct lactonization of 1,4-disubstituted 1,2,3-triazole acids through C(5)–H acyloxylation is reported. This method provides a concise and efficient pathway to synthesize lactone-fused triazole derivatives, which were obtained in good to excellent yields at room temperature.

Key words

silver-catalyzed - 1,2,3-triazoles - C(5)–H activation - acyloxylation - lactone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588779.
  • Supporting Information
 

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  • 21 General Procedure for the Synthesis of 2 1,4-Disubstituted 1,2,3-triazoles 1 (0.3 mmol), AgNO3 (5.1 mg, 0.03 mmol), KOAc (88.3 mg, 0.9 mmol), (NH4)2S2O8 (205.4 mg, 0.9 mmol), and EtOAc–H2O (1:1 v/v, 12 mL) were sequentially added to a 25 mL flask. Then the flask was stirred at r.t. for 24 h. After consumption of the 1,4-disubstitued 1,2,3-triazoles monitored by TLC analysis, H2O (15 mL) was added to the mixture and extracted with EtOAc (3 × 25 mL). The combined organic layer was washed with brine (3 × 5 mL), dried with Na2SO4, and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel with EtOAc–PE (1:8) afforded the desired product 2. 3-(p-Tolyl)-5H-benzo[d][1,2,3]triazolo[5,1-b][1,3]oxazin-5-one (2b) White solid (64 mg, 78% yield); mp 166–168 °C. 1H NMR (400 MHz, CDCl3): δ = 8.26 (dd, J = 13.4, 4.9 Hz, 2 H), 7.91 (ddd, J = 12.3, 9.4, 4.7 Hz, 3 H), 7.62–7.51 (m, 1 H), 7.24–7.18 (m, 2 H), 2.33 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 155.9, 141.0, 138.3, 137.7, 135.4, 131.5, 129.6, 128.8, 128.7, 125.5, 125.4, 115.5, 110.2, 21.3. ESI-HRMS: m/z [M + H+] calcd for C16H12N3O2: 278.0930; found: 278.0932. IR (KBr): 3672, 3060, 2960, 1760, 1600, 1482, 1379, 1263, 1095, 1010, 803, 754, 669, 450 cm–1. 3-Pentyl-5H-benzo[d][1,2,3]triazolo[5,1-b][1,3]oxazin-5-one (2r) White solid (47 mg, 61% yield); mp 59–61 °C. 1H NMR (400 MHz, CDCl3): δ = 8.31 (dd, J = 5.1, 3.6 Hz, 2 H), 8.03–7.90 (m, 1 H), 7.67–7.56 (m, 1 H), 2.86–2.71 (m, 2 H), 1.82–1.73 (m, 2 H), 1.41–1.35 (m, 4 H), 0.91 (dd, J = 9.4, 4.6 Hz, 3 H). 13CNMR (100 MHz, CDCl3): δ = 156.3, 142.0, 137.5, 135.4, 131.4, 129.7, 128.4, 115.2, 110.3, 31.3, 28.0, 23.6, 22.3, 13.9. ESI-HRMS: m/z [M + H+] calcd for C14H16N3O2: 258.1243; found: 258.1245. IR (KBr): 3666, 2927, 2861, 1774, 1693, 1613, 1517, 1448, 1379, 1228, 1144, 1003, 754, 678 cm–1.