One-Pot Synthesis of Trifluoromethylated Iodoisoxazoles via the Reaction of Trifluoroacetohydroximoyl Chloride with Terminal Alkynes and N-Iodosuccinimide

Yuwei Guo; Xiaojun Wang; Zhentong Zhu; Jianmin Zhang; Yongming Wu

doi:10.1055/s-0035-1562115

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(15): 2259-2263
DOI: 10.1055/s-0035-1562115

letter

One-Pot Synthesis of Trifluoromethylated Iodoisoxazoles via the Reaction of Trifluoroacetohydroximoyl Chloride with Terminal Alkynes and N-Iodosuccinimide

Autor*innen

Yuwei Guo

^aDepartment of Chemistry, Shanghai University, Shanghai 200444, P. R. of China eMail: jmzhang@shu.edu.cn

^bKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: ymwu@sioc.ac.cn
Xiaojun Wang

^aDepartment of Chemistry, Shanghai University, Shanghai 200444, P. R. of China eMail: jmzhang@shu.edu.cn

^bKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: ymwu@sioc.ac.cn
Zhentong Zhu

^cSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China
Jianmin Zhang*

^aDepartment of Chemistry, Shanghai University, Shanghai 200444, P. R. of China eMail: jmzhang@shu.edu.cn
Yongming Wu*

^bKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: ymwu@sioc.ac.cn

Abstract

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Abstract

Trifluoromethylated iodoisoxazoles have been synthesized by the reaction of trifluoroacetohydroximoyl chloride, alkynes, and N-iodosuccinimide in a one-pot reaction under metal-free and mild conditions. An array of iodoisoxazole compounds with a wide range of functionalities was obtained in moderate to good yields. The iodine-substituted isoxazoles render versatile reaction sites for subsequent conversion. Plausible pathways are proposed based on the control experiments.

Key words

alkynes - cycloaddition - trifluoromethylated iodoisoxazoles - hydroximoyl chloride - synthetic methods

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Referenzen

References and Notes

1a Sperry JB, Wright DL. Curr. Opin. Drug Discovery Dev. 2005; 8: 723
1b Lakhvich EV. K. F. A, Akhrem AA. Chem. Heterocycl. Compd. 1989; 25: 359

2a Müller GF, Eugster CH. Helv. Chim. Acta 1965; 48: 910
2b Takemoto T, Nakajima T, Yokobe T. J. Pharm. Soc. Jpn. 1964; 84: 1232

3a Simoni D, Rondanin R, Baruchello R. J. Med. Chem. 2008; 51: 4796
3b Daidone G, Raffa D, Maggio B, Plescia F, Cutuli VM. C, Mangano NG, Caruso A. Arch. Pharm. Pharm. Med. Chem. 1999; 332: 50
3c Van Tol HH. M, Bunzow JR, Guan HC, Sunahara RK, Seeman P, Niznik HB, Civelli O. Nature 1991; 350: 610
3d Ludden H, Pritchett DB, Kohler M, Killisch I, Keinanen K, Monyer H, Sprengel R, Seeburg PH. Nature 1990; 346: 648

4a Rowley M, Broughton HB, Collins I, Baker R, Emms F, Marwood R, Patel S, Ragan CI. J. Med. Chem. 1996; 39: 1943
4b Frølund B, Jørgensen AT, Tagmose L, Stensbøl TB, Vestergaard HT, Engblom C, Kristiansen U, Sanchez C, Krogsgaard-Larsen P, Liljefors T. J. Med. Chem. 2002; 45: 2454
4c Tomita K, Takahi Y, Ishizuka R, Kamamura S, Nakagawa M, Ando M, Nakanishi T, Udaira H. Ann. Sankyo Res. Lab. 1973; 1: 25
4d Talley J. J. Prog. Med. Chem. 1999; 13: 201

5a Martins MA. P, Siqueira GM, Bastos GP, Bonacorso HG, Zanatta N. J. Heterocycl. Chem. 1996; 33: 1619
5b Katritzky AR, Wang M, Zhang SM, Voronkov MV. J. Org. Chem. 2001; 66: 6787
5c Sloop JC, Bumgardner CL, Loehle WD. J. Fluorine Chem. 2002; 118: 135

6a Tanaka K, Masuda H, Mitsuhashi K. Bull. Chem. Soc. Jpn. 1984; 57: 2184
6b Gonçalves RS. B, Santos MD, Bernadat G, Delpon DB, Crousse B. Beilstein J. Org. Chem. 2013; 9: 2387

7a Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
7b Waldo JP, Larock RC. J. Org. Chem. 2007; 72: 9643

8a Yamazaki T, Taguchi T, Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology . Wiley-Blackwell; Chichester, UK: 2009: 1
8b Babudri F, Farinola GM, Naso F, Ragni R. Chem. Commun. 2007; 10: 1003
8c Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
8d Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
8e Harper DB, O’Hagan D. Nat. Prod. Rep. 1994; 11: 123
8f Hiyama T. Organofluorine Compounds, Chemistry and Applications. Springer; Berlin: 2000: 137
8g Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley-VCH; Weinheim: 2013. 2nd ed. 1

9a Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
9b Yang X, Wu T, Phipps RJ, Toste FD. Chem. Rev. 2015; 115: 826
9c Merino E, Nevado C. Chem. Soc. Rev. 2014; 43: 6598

10a Zhang M, Wu Y, Li Y. J. Fluorine Chem. 2006; 127: 218
10b Chen Z, Zhu J, Xie H, Li S, Wu Y, Gong Y. Adv. Synth Catal. 2010; 352: 1296
10c Chen Z, Zhu J, Xie H, Li S, Wu Y, Gong Y. Org. Lett. 2010; 12: 4376

11 Kemp MI. WO 2008135830, 2008
12 Chen W, Zhang J, Wang B, Zhao Z, Wang X, Hu Y. J. Org. Chem. 2015; 80: 2413
13 Typical Procedure for the Synthesis of Compound 4a To a dry reaction tube, 2a (147 mg, 1.0 mmol), phenylacetylene (204 mg, 2.0 mmol), NaHCO₃ (101 mg, 1.2 mmol), NIS (450 mg, 2.0 mmol), and CH₂Cl₂ (6 mL) was added successively at room temperature under N₂ atmosphere. Then the reaction was stirred at room temperature. By the end (monitored by ¹⁹F NMR), the system was diluted with water, and extracted with CH₂Cl₂ (3 × 5 mL). The combined organic extracts were dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography (hexane) affording 4a (268 mg, yield 79%); white solid; mp 102–103 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.12–7.93 (m, 2 H), 7.55 (d, J = 6.1 Hz, 3 H). ¹⁹F NMR (376 MHz, CDCl₃): δ = –63.67 (s, 3 F). ¹³C NMR (101 MHz, CDCl₃): δ = 171.35 (s), 157.56 (q, J = 36.5 Hz), 131.70 (s), 129.09 (s), 127.92 (s), 126.03 (s), 119.41 (q, J = 272.5 Hz), 49.70 (s). HRMS (EI): m/z calcd for C₁₀H₅F₃INO [M]⁺: 338.9368; found: 338.9362. IR (KBr): ν = 2956, 1476, 1446, 1255, 1187, 1143, 1006, 960 cm^–1.
14 Jiang Q, Wang J, Guo C. Synthesis 2015; 47: 2081
15 Waldo JP, Mehta S, Neuenswander B, Lushington GH, Larock RC. J. Comb. Chem. 2008; 10: 658

Zusatzmaterial

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