Synthesis of perfluoroalkyl-substituted γ-lactones and 4,5-dihydropyridazin-3(2H)-ones via donor-acceptor cyclopropanes

Helvetica Chimica Acta

Volumn 95, Issue 10, 2012, Pages 1818-1830

  Gladow, Daniel ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Donor acceptor cyclopropanes; Fluorine compounds; Heterocycles, fluorinated; Lactones; Pyridazinones; Silyl enol ethers, perfluoroalkyl substituted

Indexed keywords

DONOR-ACCEPTORS; HETEROCYCLES; LACTONES; PYRIDAZINONES; SILYL ENOL ETHERS;

ESTERIFICATION; ETHERS; FLUORINE; FLUORINE COMPOUNDS; PROPANE; RHODIUM;

ESTERS;

4,5 DIHYDRO 2 PHENYL 4 (TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 2 PHENYL 4,6 BIS(TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 2 PHENYL 6 (TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 2 PHENYL 6 (UNDECAFLUOROPENTYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 3 (TRIFLUOROMETHYL)FURAN 2(3H)ONE; 4,5 DIHYDRO 3,5 BIS(TRIFLUOROMETHYL)FURAN 2(3H)ONE; 4,5 DIHYDRO 4 (TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 4,6 BIS(TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 5 (TRIFLUOROMETHYL)FURAN 2(3H)ONE; 4,5 DIHYDRO 5 (UNDECAFLUOROPENTYL)FURAN 2(3H)ONE; 4,5 DIHYDRO 6 (PENTAFLUOROPHENYL) 2 PHENYLPYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 6 (PENTAFLUOROPHENYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 6 (TRIFLUOROMETHYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDRO 6 (UNDECAFLUOROPENTYL)PYRIDAZIN 3(2H)ONE; 4,5 DIHYDROPYRIDAZIN 3(2H)ONE DERIVATIVE; CYCLOPROPANE DERIVATIVE; ETHYL 1 (TRIFLUOROMETHYL) 2 [(TRIMETHYLSILYL)OXY] 2 (UNDECAFLUOROPENTYL)CYCLOPROPANECARBOXYLATE; ETHYL 1 (TRIFLUOROMETHYL) 2 [(TRIMETHYLSILYL)OXY]CYCLOPROPANECARBOXYLATE; ETHYL 1,2 BIS(TRIFLUOROMETHYL) 2 [(TRIMETHYLSILYL)OXY]CYCLOPROPANECARBOXYLATE; ETHYL 3,3,3 TRIFLUORO 2 (1H INDOL 3 YL)PROPANOATE; ETHYL 4 HYDROXY 2 (TRIFLUOROMETHYL)BUTANOATE; FLUORINE DERIVATIVE; GAMMA LACTONE DERIVATIVE; METHYL 2 (PENTAFLUOROPHENYL) 2 [(TRIMETHYLSILYL)OXY]CYCLOPROPANECARBOXYLATE; METHYL 2 (TRIFLUOROMETHYL) 2 [(TRIMETHYLSILYL)OXY]CYCLOPROPANECARBOXYLATE; METHYL 2 [(TRIMETHYLSILYL)OXY] 2 (UNDECAFLUOROPENTYL)CYCLOPROPANECARBOXYLATE; METHYL 5,5,5 TRIFLUORO 4 HYDROXYPENTANOATE; METHYL 5,5,6,6,7,7,8,8,9,9,9 UNDECAFLUORO 4 HYDROXYNONANOATE; PERFLUOROALKYL DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ONE POT SYNTHESIS; PRIORITY JOURNAL; REDUCTION KINETICS; SUBSTITUTION REACTION;

EID: 84867733548     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200413     Document Type: Article

References (72)

1. D. Seebach, Angew. Chem. 1979, 91, 259
2. D. Seebach, Angew. Chem., Int. Ed. 1979, 18, 239
3. D. Wendisch, 'Carbocyclic Three-Membered Ring Compounds', in 'Methods in Organic Chemistry (Houben-Weyl)', Vol. 4/3, 4th edn., Ed. E. Müller, Thieme, Stuttgart, 1971, p. 879
4. D. Seebach, S. Beckmann, H. Geiger, 'Isocyclic Four-Membered Ring Compounds', in 'Methods in Organic Chemistry (Houben-Weyl)', Vol. 4/4, 4th edn., Ed. E. Müller, Thieme, 1971, p. 567
5. S. Danishefsky, Acc. Chem. Res. 1979, 12, 66
6. H.-U. Reissig, 'The Chemistry of the Cyclopropyl Group', in 'Organic Synthesis via Cyclopropanes-Principles and Applications', Ed. Z. Rappoport, John Wiley and Sons, London, 1987, pp. 375-443
7. H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165
8. A. de Meijere, 'Carbocyclic Three- and Four-Membered Ring Compounds', in 'Methods in Organic Chemistry (Houben-Weyl)', Vol. E17a-d, Thieme, Stuttgart, 1997
9. A. de Meijere, S. I. Kozhushkov, 'Product Class 2: Cyclopropanes', in 'Alkanes', 'Science of Synthesis', Vol. 48, Ed. I. Fleming, Thieme, Stuttgart, 2009, pp. 477-613
10. R. Kostikov, M. S. Baird, in 'Product Class 3: Cyclobutanes', in 'Alkanes', 'Science of Synthesis', Vol. 48, Ed. I. Fleming, Thieme, Stuttgart, 2009, pp. 615-646.
11. E. Wenkert, Acc. Chem. Res. 1980, 13, 27.
12. H.-U. Reissig, E. Hirsch, Angew. Chem. 1980, 92, 839
13. H.-U. Reissig, E. Hirsch, Angew. Chem., Int. Ed. 1980, 19, 813.
14. H.-U. Reissig, Top. Curr. Chem. 1988, 144, 73
15. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151
16. F. Gnad, O. Reiser, Chem. Rev. 2003, 103, 1603
17. M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321
18. F. De Simone, J. Waser, Synthesis 2009, 3353
19. T. F. Schneider, D. B. Werz, Org. Lett. 2011, 13, 1848
20. M. Y. Mel'nikov, E. M. Budynina, O. A. Ivanova, I. V. Trushkov, Mendeleev Commun. 2011, 21, 293.
21. C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051
22. M. J. Campbell, J. S. Johnson, A. T. Parsons, P. D. Pohlhaus, S. D. Sanders, J. Org. Chem. 2010, 75, 6317
23. T. F. Schneider, J. Kaschel, S. I. Awan, B. Dittrich, D. B. Werz, Chem.-Eur. J. 2010, 16, 11276
24. T. P. Lebold, M. A. Kerr, Pure Appl. Chem. 2010, 82, 1797.
25. O. O. Grygorenko, O. S. Artamonov, I. V. Komarov, P. K. Mykhailiuk, Tetrahedron 2011, 67, 803
26. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 950
27. B. Morandi, E. M. Carreira, Angew. Chem., Int. Ed. 2010, 49, 938
28. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 4390
29. B. Morandi, E. M. Carreira, Angew. Chem., Int. Ed. 2010, 49, 4294
30. B. Morandi, J. Cheang, E. M. Carreira, Org. Lett. 2011, 13, 3080
31. V. R. Petrov, W. Marshall, J. Fluorine Chem. 2012, 133, 61.
32. T. Hiyama, 'Organofluorine Compounds: Chemistry and Applications', Springer, Berlin Heidelberg, 2000
33. P. Kirsch, 'Modern Fluoroorganic Chemistry', Wiley-VCH, Weinheim, 2005
34. K. Müller, C. Fäh, F. Diederich, Science 2007, 317, 1881
35. D. O' Hagan, Chem. Soc. Rev. 2008, 37, 308
36. T. Yamazaki, T. Taguchi, I. Ojima, in 'Fluorine in Medicinal Chemistry and Chemical Biology', Ed. I. Ojima, Wiley-Blackwell, Chichester, 2009, pp. 3-46
37. A. A. Gakh, L. K. Kirk, 'Fluorinated Heterocycles', American Chemical Society, Washington, 2009
38. V. A. Petrov, 'Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications', John Wiley & Sons, Hoboken, 2009.
39. S. Gil, M. Parra, P. Rodriguez, J. Segura, Mini-Rev. Org. Chem. 2009, 6, 345
40. M. Seitz, O. Reiser, Curr. Opin. Chem. Biol. 2005, 9, 285
41. E. M. Maier, in 'Three Carbon-Heteroatom Bonds: Esters and Lactones; Peroxyacids and R(CO)OX Compounds; R(CO)X, X=S, Se, Te', 'Science of Synthesis, Houben-Weyl Methods of Molecular Transformations', Eds. J. S. Panek, E. N. Jacobsen, Thieme, Stuttgart, 2006, Vol. 20b, pp. 1421-1551.
42. W. Adam, J.-C. Liu, O. Rodriguez, J. Org. Chem. 1973, 38, 2269
43. T. Kitazume, N. Ishikawa, Chem. Lett. 1984, 13, 1815
44. D. Seebach, P. Renaud, W. B. Schweizer, M. F. Züger, M.-J. Brienne, Helv. Chim. Acta 1984, 67, 1843
45. D. Seebach, P. Renaud, Helv. Chim. Acta 1985, 68, 2342
46. M. Acs, C. von dem Bussche, D. Seebach, Chimia 1990, 44, 90
47. C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795
48. M. Gautschi, W. B. Schweizer, D. Seebach, Chem. Ber. 1994, 127, 565
49. A. R. Sting, D. Seebach, Tetrahedron 1996, 52, 279
50. H. Angert, R. Czerwonka, H.-U. Reissig, Liebigs Ann. 1997, 2215
51. F.-L. Qing, Z.-X. Jiang, Tetrahedron Lett. 2001, 42, 5933.
52. M. Tišler, B. Stanovnik, Adv. Heterocycl. Chem. 1968, 9, 211
53. F. R. Rittig, R. Becker, H. Bleiholder, F. Feichtmayr, E. Haedicke, J. B. S. John, Pestic. Sci. 1983, 14, 299
54. P. Máatyus, J. Heterocycl. Chem. 1998, 35, 1075
55. S.-G. Lee, J.-J. Kim, H.-K. Kim, D.-H. Kweon, Y.-J. Kang, S.-D. Cho, S.-K. Kim, Y.-J. Yoon, Curr. Org. Chem. 2004, 8, 1463.
56. E. Fischer, Justus Liebigs Ann. Chem. 1886, 236, 126.
57. E. L. Grimm, H.-U. Reissig, J. Org. Chem. 1985, 50, 242.
58. I. Reichelt, H.-U. Reissig, Synthesis 1984, 786.
59. E. L. Grimm, R. Zschiesche, H.-U. Reissig, J. Org. Chem. 1985, 50, 5543
60. A. Ullmann, J. Schnaubelt, H.-U. Reissig, Synthesis 1998, 1052
61. R. Zimmer, A. Ziemer, M. Gruner, I. Brüdgam, H. Hartl, H.-U. Reissig, Synthesis 2001, 1649
62. P. K. Patra, H.-U. Reissig, Eur. J. Org. Chem. 2001, 4195
63. I. Veljkovic, R. Zimmer, H.-U. Reissig, I. Brüdgam, H. Hartl, Synthesis 2006, 2677
64. H. Ãzbek, I. S. Veljkovic, H.-U. Reissig, Synlett 2008, 3145.
65. W. Wan, J. Hou, H. Jiang, Y. Wang, S. Zhu, H. Deng, J. Hao, Tetrahedron 2009, 65, 4212.
66. H. A. Laub, D. Gladow, H.-U. Reissig, H. Mayr, Org. Lett. 2012, 14, 3990.
67. E. B. Womack, A. B. Nelson, Org. Synth., Coll. Vol. 1955, 3, 392
68. E. B. Womack, A. B. Nelson, Org. Synth. 1944, 24, 56.
69. G. Shi, Y. Xu, J. Chem. Soc., Chem. Commun. 1989, 607.
70. R. H. Groth, J. Org. Chem. 1959, 24, 1709
71. M. Hanack, H. Meyer, Justus Liebigs Ann. Chem. 1968, 720, 81.
72. R. E. Brown, F. Burkamp, V. A. Doughty, S. R. Fletcher, G. J. Hollingworth, B. A. Jones, T. J. Sparey, WO2004074290A1, 2004.