Synthesis of CF3-Containing 1,2,3,4-Tetrahydroisoquinoline-3-Phosphonates via Regioselective Ruthenium-Catalyzed Co-cyclotrimerization of 1,7-Aza­diynes

Maria A. Zotova; Daria V. Vorobyeva; Pierre H. Dixneuf; Christian Bruneau; Sergey N. Osipov

doi:10.1055/s-0033-1339173

Synlett, Table of Contents

Synlett 2013; 24(12): 1517-1522
DOI: 10.1055/s-0033-1339173

letter

Synthesis of CF₃-Containing 1,2,3,4-Tetrahydroisoquinoline-3-Phosphonates via Regioselective Ruthenium-Catalyzed Co-cyclotrimerization of 1,7-Azadiynes

Maria A. Zotova

^aA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia Fax: +7(499)1355085 Email: osipov@ineos.ac.ru

,

Daria V. Vorobyeva

^aA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia Fax: +7(499)1355085 Email: osipov@ineos.ac.ru

,

Pierre H. Dixneuf

^bCentre of Catalysis and Green Chemistry, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France

,

Christian Bruneau

^bCentre of Catalysis and Green Chemistry, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France

,

Sergey N. Osipov*

^aA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia Fax: +7(499)1355085 Email: osipov@ineos.ac.ru

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Abstract

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Abstract

An efficient access to novel trifluoromethyl-substituted phosphonate analogues of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (TIC) derivatives based on regioselective ruthenium-catalyzed co-cyclotrimerization of functionalized 1,7-diynes with various alkynes has been developed using RuClCp*cod and preferably Grubbs second-generation catalysts.

Key words

α-aminophosphonates - 1,7-azadiynes - alkynes - cyclotrimerization - ruthenium catalysis

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References

References and Notes

1a Aminophosphonic and Aminophosphinic Acids – Chemistry and Biological Activity. Kuhkhar VP, Hudson HR. Wiley; Chichester: 2000
1b Ordonez M, Sayago FJ, Cativiela C. Tetrahedron 2012; 68: 6369

2a Troev KD. Chemistry and Application of H-Phosphonates. Elsevier; Amsterdam: 2006
2b Naydenova ED, Todorov PT, Troev KD. Amino Acids 2010; 38: 23

3a Kafarski P, Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 63: 193
3b Hiratake J, Oda J. Biosci. Biotechnol. Biochem. 1997; 61: 211
3c Alonso E, Solis A, del Pozo C. Synlett 2000; 698
3d Kafarski P, Lejczak B. Curr. Med. Chem. 2001; 1: 301

4 Smith AB. III, Yager KM, Taylor CM. J. Am. Chem. Soc. 1995; 117: 10879
5 Hirschmann R, Smith AB. III, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengeler PA, Benkovic SJ. Science 1994; 265: 234

6a Allen JG, Atherton FR, Hall MJ, Hassal CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. Nature (London) 1978; 272: 56
6b Atherton FR, Hassall CH, Lambert RW. J. Med. Chem. 1986; 29: 29

7 Reddy SS, Sankar AU. R, Raju CN, Rao VK. S. Afr. J. Chem. 2008; 61: 97
8 Maier L, Diel PJ. Phosphorus Sulfur Silicon Relat. Elem. 1991; 57: 57
9 Gavras I, Vlahakos D, Melby JC, Gavras H. J. Clin. Pharm. 1984; 24: 343
10 Asaoka T, Yazawa K, Mikami Y, Takahashi K. J. Antibiot. 1982; 35: 1708
11 Francois G, Bringmann G, Phillipson JD, Boyd MR, Assi LA, Schneider C, Timperman G. US 5,639,761, 1994

12a Otake K, Azukizawa S, Fukui M, Kunishiro K, Kamemoto H, Kanda M, Miike T, Kasai M, Shirahase H. Bioorg. Med. Chem. 2012; 20: 1060
12b Vendeville S, Goossens F, Debreu-Fontaine MA, Landry V, Davioud-Charvet E, Grellier P, Scharpe S, Sergheraert G. Bioorg. Med. Chem. 2002; 10: 1719
12c Matter H, Schudok M, Schwab W, Thorwart W, Barbier D, Billen G, Haase B, Neises B, Weithmann KU, Wollmann T. Bioorg. Med. Chem. 2002; 10: 3529
12d Zhang Y, Feng J, Jia Y, Wang X, Zhang L, Liu C, Fang H, Xu W. J. Med. Chem. 2011; 54: 2823

13 Wang A, U’Prichard DC, Marder VJ. US 0061885 A1, 2002

14a Balboni G, Fiorini S, Baldisserotto A, Trapella C, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S. J. Med. Chem. 2008; 51: 5109
14b Ballet S, Feytens D, De Wachter R, De Vlaeminck M, Marczak ED, Salvadori S, de Graaf C, Rognan D, Negri L, Lattanzi R, Lazarus LH, Tourwé D, Balboni G. Bioorg. Med. Chem. Lett. 2009; 19: 433

15 Markina NA, Mancuso R, Neuenswander B, Lushington GH, Larock RC. ACS Comb. Sci. 2011; 13: 265

16a Kirsch P. Modern Fluoroorganic Chemistry . Wiley-VCH; Weinheim: 2004
16b Uneyama K. Organofluorine Chemistry . Blackwell; Oxford: 2006
16c Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology. Wiley-Blackwell; Chichester: 2009
16d Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
16e Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
16f Hird M. Chem. Soc. Rev. 2007; 36: 2070
16g Kirk KL. Org. Process Res. Dev. 2008; 12: 305
16h O’Hagan D. Chem. Soc. Rev. 2008; 37: 308

17a Lundgren RJ, Stradiotto M. Angew. Chem. Int. Ed. 2010; 49: 9322
17b Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455

18 Shchetnikov GT, Osipov SN, Bruneau C, Dixneuf PH. Synlett 2008; 578
19 Zotova MA, Vasilyeva TP, Peregudov AS, Osipov SN. J. Fluorine Chem. 2012; 135: 33

Related access to nonfluorinated TIC-derivatives:

20a Kotha S, Sreenivasachary N. Eur. J. Org. Chem. 2001; 3375
20b Kotha S, Banerjee S. Synthesis 2007; 1015

Selected papers on Ru-catalyzed alkyne cyclotrimerization:

21a Yamamoto Y, Kitahara H, Ogawa R, Itoh K. J. Org. Chem. 1998; 63: 9610
21b Yamamoto Y, Ogawa R, Itoh K. Chem. Commun. 2000; 549
21c Yamamoto Y, Arakawa T, Ogawa R, Itoh K. J. Am. Chem. Soc. 2003; 125: 12143
21d Saito S, Yamamoto Y. Chem. Rev. 2000; 100: 2901

22a Kirchner K, Calhorda MJ, Schmid R, Veiros LF. J. Am. Chem. Soc. 2003; 125: 11721
22b Paih JL, Monnier F, Dérien S, Dixneuf PH, Clot E, Eisenstein O. J. Am. Chem. Soc. 2003; 125: 11964
22c Le Paih J, Dérien S, Demerseman B, Bruneau C, Dixneuf PH, Toupet L, Dazinger G, Kirchner K. Chem. Eur. J. 2005; 11: 1312

23a Peters J.-U, Blechert S. Chem. Commun. 1997; 1983
23b Witulski B, Stengel T, Fernández-Hernández JM. Chem. Commun. 2000; 1965

24 Typical Procedure for Compound 6 A degased solution of dyine-containing aminophosphonate (0.39 mmol), alkyne (1.55 mmol, 4 equiv), and Grubbs II catalyst (0.02 mmol, 5 mol%) in dry CH₂Cl₂ (8 mL) was stirred under heating at 60 °C for 3 h. After cooling to r.t., the solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel (eluent: CH₂Cl₂–EtOAc) to afford the product. Selected Data for Compound 6b ¹H NMR (300 MHz, CDCl₃): δ = 0.98 (t, J = 7.3 Hz, 3 H, CH₃), 1.07 (t, J = 7.1 Hz, 3 H, CH₃), 1.17 (t, J = 6.5 Hz, 3 H, CH₃), 1.32–1.45 (m, 2 H, CH₂), 1.61–1.71 (m, 2 H, CH₂), 2.68 (t, J = 7.6 Hz, 2 H, CH₂), 3.52–3.56 (m, 2 H, CH₂), 3.89–4.20 (m, 4 H, OCH₂), 4.76 (br s, 2 H, CH₂), 5.21 (d, J = 12.2 Hz, 1 H, OCH₂), 5.35 (d, J = 12.2 Hz, 1 H, OCH₂), 7.08–7.21 (m, 2 H, ArH), 7.32–7.52 (m, 10 H, ArH). ¹⁹F NMR (282 MHz, CDCl₃): δ = 9.81 (s, 3 F, CF₃). ³¹P NMR (161 MHz, CDCl₃): δ = 16.63 (q, J = 3.3 Hz). ¹³C NMR (151 MHz, CDCl₃): δ = 13.9, 15.8 (d, J = 6.6 Hz), 16.2 (d, J = 5.5 Hz), 22.4, 33.6, 35.3, 43.4, 47.3, 62.7 (d, J = 8.8 Hz), 64.0 (m), 64.8 (dq, J = 28.7, 154.8 Hz), 67.9, 124.7, 125.9 (qd, J = 12.8, 288.9 Hz), 127.1, 127.2 (d, J = 6.6 Hz), 128.1, 128.2, 128.3, 128.4, 129.2, 129.4, 136.2, 140.2, 140.6, 141.6, 155.7, 171.1. Anal. Calcd for C₃₂H₃₇F₃NO₅P: C, 63.67; H, 6.18; N, 2.32. Found: C, 63.28; H, 5.88; N, 2.54

Supplementary Material

Supporting Information

Synthesis of CF3-Containing 1,2,3,4-Tetrahydroisoquinoline-3-Phosphonates via Regioselective Ruthenium-Catalyzed Co-cyclotrimerization of 1,7-Aza­diynes

Synthesis of CF₃-Containing 1,2,3,4-Tetrahydroisoquinoline-3-Phosphonates via Regioselective Ruthenium-Catalyzed Co-cyclotrimerization of 1,7-Azadiynes