Use of 3-(Pentafluorosulfanyl)phenol to Access to Advanced Substituted Pentafluorosulfanylphenol/anisole: Application to the Synthesis of 2-(Arylpentafluorosulfanyl)indanedione

Page: [602 - 607] Pages: 6

  • * (Excluding Mailing and Handling)

Abstract

The synthesis of advanced substituted 3-pentafluorosulfanylphenol/anisole was accomplished starting from the easy to access and commercially available 3-pentafluorosulfanylphenol. These products bear diverse substitutions such as ester, aldehyde, halogens, alcohol, nitrile and carboxylic acid and could be in the future used as high-value building blocks for the synthesis of various scaffolds. For our part, this intermediate had been used to synthesize a library of 2-arylindadiones substituted by a pentafluorosulfanyl group.

Keywords: SF5, pentafluorosulfanyl, indanedione, anisole, phenol, building blocks.

Graphical Abstract

[1]
Savoie, P.R.; Welch, J.T. Chem. Rev., 2015, 115(2), 1130-1190.
[http://dx.doi.org/10.1021/cr500336u] [PMID: 25341449]
[2]
(a) Sheppard, W.A. J. Am. Chem. Soc., 1962, 84, 3064-3072.
[http://dx.doi.org/10.1021/ja00875a006]
(b) Browden, R.D.; Comina, P.J.; Greenhall, M.P.; Kariuki, B.M.; Loveday, A.; Philp, D. Tetrahedron, 2000, 56, 3399-3408.
[http://dx.doi.org/10.1016/S0040-4020(00)00184-8]
Nenajdenko, V. Fluorine in Heterocyclic Chemistry., 2014. Vol. 1
[3]
Hansch, C.; Muir, R.M.; Fujita, T.; Maloney, P.P.; Geiger, F.; Streich, M. J. Am. Chem. Soc., 1963, 85, 2817-2824.
[http://dx.doi.org/10.1021/ja00901a033]
[4]
Saethre, L.J.; Berrah, N.; Bozek, J.D. BA,rve, K.J.; Carroll, T.X.; Kukk, E.; Gard, G.L.; Winter, R.; Thomas, T.D. J. Am. Chem. Soc., 2001, 123(43), 10729-10737.
[http://dx.doi.org/10.1021/ja016395j] [PMID: 11674006]
[5]
Sowaileh, M.F.; Hazlitt, R.A.; Colby, D.A. Chem. Med. Chem., 2017, 12(18), 1481-1490.
[http://dx.doi.org/10.1002/cmdc.201700356] [PMID: 28782186]
[6]
In particular Fluindione (Previscan®), Anisindione and Phenindione which are vitamin K antagonists (VKA) and anticoagulents.,
[7]
Leroux, F.R.; Manteau, B.; Vors, J-P.; Pazenok, S. Beilstein J. Org. Chem., 2008, 4, 13.
[http://dx.doi.org/10.3762/bjoc.4.13] [PMID: 18941485]
[8]
Zhang, Y.; Wang, Y.; He, C.; Liu, X.; Lu, Y.; Chen, T.; Pan, Q.; Xiong, J.; She, M.; Tu, Z.; Qin, X.; Li, M.; Tortorella, M.D.; Talley, J.J. J. Med. Chem., 2017, 60(10), 4135-4146.
[http://dx.doi.org/10.1021/acs.jmedchem.6b01484] [PMID: 28475316]
[9]
Wang, L.; Wang, Y.; Guo, F.; Zheng, Y.; Bhadury, P.S.; Sun, Z. Tetrahedron Lett., 2013, 54, 6053-6056.
[http://dx.doi.org/10.1016/j.tetlet.2013.08.098]
[10]
(a) Kirsch, P.; Bremer, M.; Heckmeier, M.; Tarumi, K. Angew. Chem. Int. Ed., 1999, 38, 1989-1992. http://dx.doi.org/10.1002/(SICI)1521-3773(19990712)38: 13/14<1989::AID-ANIE1989>3.0.CO;2-K
(b) Kleemann Pentafluorosulfanylbenzoylguanidines, H-W. U.S. Patent US 20030216476A1, 2003.
[11]
Shi, G.Q.; Dropinski, J.F.; Zhang, Y.; Santini, C.; Sahoo, S.P.; Berger, J.P.; Macnaul, K.L.; Zhou, G.; Agrawal, A.; Alvaro, R.; Cai, T.Q.; Hernandez, M.; Wright, S.D.; Moller, D.E.; Heck, J.V.; Meinke, P.T. J. Med. Chem., 2005, 48(17), 5589-5599.
[http://dx.doi.org/10.1021/jm050373g] [PMID: 16107159]
[12]
Aikawa, K.; Miyazaki, Y.; Mikami, K. Bull. Chem. Soc. Jpn., 2012, 85, 201-208.
[http://dx.doi.org/10.1246/bcsj.20110309]
[13]
Frischmuth, A.; Unsinn, A.; Groll, K. StadtmA1/4ller, H.; Knochel, P. Chemistry, 2012, 18(33), 10234-10238.
[http://dx.doi.org/10.1002/chem.201201485] [PMID: 22714685]
[14]
Ali, A.; Lu, Z.; Sinclair, P.J.; Chen, Y-H.; Smith, C.J.; Li, H. WO Patent 2007079186 A2, 2007.
[15]
(a) Oldenziel, O.H.; Van Leusen, D.; Van Leusen, A.M. J. Org. Chem., 1977, 42, 3114-3118.
[http://dx.doi.org/10.1021/jo00439a002]
(b) Perner, R.J.; Koenig, J.R.; Didomenico, S.; Bayburt, E.K.; Daanen, J.F.; Gomtsyan, A.R.; Kort, M.E.; Kym, P.R.; Vasudevan, A.; Schmidt, R.G.; Voight, E. Patent WO 2009055749 A, 2009.
[16]
Nikulin, V.I.; Pisarenko, L.M. Izvestiya Akademii Nauk SSSR.Seriya Khimicheskaya; , 1986, 8, pp. 1850-1855.
[17]
Sik, J.Y.; Kgo, L.C. WO Patent 2012173447 A2, 2012.
[18]
(a) Nikulin, V.I.; Pisarenko, L.M. 1986, 3, 637-640.
(b) Veith, R.; Henke, H.; Aldag, R.; Braun, M. Chem. Ber., 1987, 120, 265-268.
[http://dx.doi.org/10.1002/cber.19871200303]