Fluorinated heterocyclic compounds. An expedient route to 5-perfluoroalkyl-1,2,4-triazoles via an unusual hydrazinolysis of 5-perfluoroalkyl-1,2,4-oxadiazoles: First examples of an ANRORC-like reaction in 1,2,4-oxadiazole derivatives

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 605-608

  Buscemi, Silvestre ^a   Pace, Andrea ^a   Pibiri, Ivana ^a   Vivona, Nicolò ^a   Spinelli, Domenico ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; FLUORINE COMPOUNDS; NITROGEN; RING OPENING POLYMERIZATION;

NUCLEOPHILIC ADDITION;

AROMATIC COMPOUNDS;

1,2,4 OXADIAZOLE DERIVATIVE; 1,2,4 TRIAZOLE DERIVATIVE; 5 TRIFLUOROMETHYL 3 UNDECYL 1,2,4 OXADIAZOLE; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE; METHYLHYDRAZINE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FLUORINATION; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037462414     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0262762     Document Type: Article

References (58)

1. (a) Chambers, R. D.; Sargent, C. R. Adv. Heterocycl. Chem. 1981, 28, 1-71.
2. (b) Silvester, M. J. Adv. Heterocycl. Chem. 1994, 59, 1-38.
3. (c) Burger, K.; Wucherpfennig, U.; Brunner, E. Adv. Heterocycl. Chem. 1994, 60, 1-64.
4. Furin, G. G. Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Roma, 1998; Vol. 2, pp 355-441.
5. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
6. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
7. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
8. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
9. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
10. For heterocyclic rearrangements, see: (a) Van der Plas, H. C. Ring Transformations of heterocycles; Academic: New York, 1973; Vols. 1 and 2. (b) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007. (c) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320. (d) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169. (e) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638. (f) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
11. Van der Plas, H. C. Adv. Heterocycl. Chem. 1999, 74, 1-253.
12. For photoinduced rearrangements of five-membered heterocycles, see: (a) Padwa, A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 501-547. (b) D'Auria, M. Heterocycles 1999, 50, 1115-1135, (c) D'Auria, M. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Società Chimica Italiana: Roma, 1999; Vol. 2, pp 233-279. (d) D'Auria, M. Adv. Heterocycl, Chem, 2001, 79, 41-88.
13. For photoinduced rearrangements of five-membered heterocycles, see: (a) Padwa, A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 501-547. (b) D'Auria, M. Heterocycles 1999, 50, 1115-1135, (c) D'Auria, M. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Società Chimica Italiana: Roma, 1999; Vol. 2, pp 233-279. (d) D'Auria, M. Adv. Heterocycl, Chem, 2001, 79, 41-88.
14. For photoinduced rearrangements of five-membered heterocycles, see: (a) Padwa, A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 501-547. (b) D'Auria, M. Heterocycles 1999, 50, 1115-1135, (c) D'Auria, M. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Società Chimica Italiana: Roma, 1999; Vol. 2, pp 233-279. (d) D'Auria, M. Adv. Heterocycl, Chem, 2001, 79, 41-88.
15. For photoinduced rearrangements of five-membered heterocycles, see: (a) Padwa, A. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 501-547. (b) D'Auria, M. Heterocycles 1999, 50, 1115-1135, (c) D'Auria, M. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Società Chimica Italiana: Roma, 1999; Vol. 2, pp 233-279. (d) D'Auria, M. Adv. Heterocycl, Chem, 2001, 79, 41-88.
16. (a) Buscemi, S.; Pace, A.; Vivona, N. Tetrahedron Lett, 2000, 41, 7977-7981.
17. (b) Buscemi, S.; Pace, A.; Calabrese, R.; Vivona, N.; Metrangolo P. Tetrahedron 2001, 57, 5865-5871.
18. (a) Dickinson, R. G.; Jacobsen, N. W. Aust. J. Chem. 1975, 28, 2435-2446.
19. (b) Rykowski, A.; Wolinska, E. Tetrahedron Lett. 1996, 37, 5795-5796.
20. (c) Rykowski, A.; Branowska, D. Heterocycles 1996, 43, 2095-2098.
21. (d) Chupakhin, O. N.; Kozhevnikov, V. N.; Kozhevnikov, D. N.; Rusinov, V. L. Tetrahedron Lett, 1999, 40, 6099-6100.
22. (e) Chupakhin, O. N.; Kozhevnikov, V. N.; Prokhorov, A. M.; Kozhevnikov, D. N.; Rusinov, V. L. Tetrahedron Lett. 2000, 41, 7379-7382.
23. (a) Hetzheim, A.; Mockel, K. Adv. Heterocycl. Chem. 1966, 7, 183-224.
24. (b) Reid, J. R.; Heindel, N. D. J. Heterocycl. Chem. 1976, 13, 925-926.
25. Sandstrom, J. Adv. Heterocycl. Chem. 1968, 9, 165-209.
26. Suwinski, J.; Pawlus, W.; Salwinska, E.; Swierczek, K. Heterocycles 1994, 37, 1511-1520.
27. (a) Reitz, D. B.; Finkes, M. J. J. Heterocycl. Chem. 1989, 26, 225-230.
28. (b) Reitz, D. B.; Finkes, M. J. J. Org. Chem. 1989, 54, 1760-1762.
29. (b) Critchley, J. P.; Pippett, J. S. J. Fluorine Chem. 1973, 2, 137-156.
30. For mechanistic studies on azole-to-azole interconversion reactions of the Boulton-Katritzky-type, see: Cosimelli, B.; Guernelli, S.; Spinelli, D.; Buscemi, S.; Frenna, V.; Macaluso, G. J. Org. Chem. 2001, 66, 6124-6129 and references therein for several papers on this series from the Spinelli research group.
31. (a) Vivona, N.; Buscemi, S. Heterocycles 1995, 41, 2095-2116 and references therein.
32. (b) Buscemi, S.; Vivona, N.; Caronna, T. J. Org. Chem. 1995, 60, 4096-4101.
33. (c) Buscemi, S.; Vivona, N.; Caronna, T. J. Org. Chem. 1996, 61, 8397-8401.
34. (d) Vivona, N.; Buscemi, S.; Asta, S.; Caronna, T. Tetrahedron 1997, 53, 12629-12636.
35. (e) Buscemi, S.; Pace, A.; Vivona, N.; Caronna, T.; Galia, A. J. Org. Chem. 1999, 64, 7028-7033.
36. (f) Buscemi, S.; Pace, A.; Vivona, N.; Caronna, T. J. Heterocycl. Chem. 2001, 38, 777-780.
37. (g) Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N. J. Org. Chem. 2002, 67, 6253-6255.
38. Jochims, J. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds; Pergamon: Elsevier Science, 1996; Vol. 4, pp 179-228.
39. Differently from 3,5-disubstituted 1,2,4-oxadiazoles, monosubstituted derivatives are markedly less stable under hydrolytic conditions.
40. (a) Andrianov, V. G.; Eremev, A. V.; Sheremet, Yu. B. Chem. Heterocycl. Compd. (Engl. Transl.) 1988, 24, 707.
41. (b) Andrianov, V. G.; Semenikhina, V. G.; Eremev, A. V. Chem. Heterocycl. Compd. (Engl. Transl.) 1991, 27, 651-656.
42. Differently from 5-trichloromethyl-1,2,4-oxadiazoles, for which displacement of the trichloromethyl group has been observed under the influence of nucleophiles, bis(5-trifluoromethyl-1,2,4-oxadiazol-3-y1) reacts with alcoholic potassium or sodium hydroxide furnishing stable anionic σ-adducts [Andrianov, V. G.; Eremev, A. V. Chem. Heterocycl. Compd. (Engl. Transl.) 1990, 26, 714].
43. Exner, O. Correlation Analysis of Chemical Data; Plenum Press: New York, 1988.
44. (a) Buscemi, S.; Pace, A.; Frenna, V.; Vivona, N. Heterocycles 2002, 57, 811-823.
45. (b) Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N. Heterocycles 2002, 57, 1891-1896.
46. Funabiki, K.; Noma, N.; Kuzuya, G.; Matsui, M.; Shibata, K. J. Chem. Res., Synop. 1999, 300-301; J. Chem. Res., Miniprint 1999, 1301-1308 and references therein for recent literature on fluorinated 1,2,4-triazoles.
47. Funabiki, K.; Noma, N.; Kuzuya, G.; Matsui, M.; Shibata, K. J. Chem. Res., Synop. 1999, 300-301; J. Chem. Res., Miniprint 1999, 1301-1308 and references therein for recent literature on fluorinated 1,2,4-triazoles.
48. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, Germany, 1988.
49. (a) Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents. In Techniques of Chemistry, 4th ed.; Weissberger, A., Ed.; Wiley-Interscience: New York, 1986; Vol. 2.
50. (b) Maryott, A. A.; Smith, E. R. Table of Dielectric Constants of Pure Liquids; NBS Circular 514; National Bureau of Standards: Washington, DC, 1951.
51. (a) Schmid, R. J. Sol. Chem. 1983, 12, 135-152.
52. (b) Marcus, Y. J. Sol. Chem. 1984, 13, 599-624.
53. Reichardt, C.; Harbusch-Görnert, E. Liebigs Ann. Chem. 1983, 721-743.
54. In the hydrazinolysis reaction carried out in DMF, significant competition of the formed hydroxylamine (as a bidentate nucleophile) towards the attack at C(5) of the starting oxadiazole was observed to some extent, depending on the substrate and on the molar ratio of the reagents. This peculiar aspect of the reactivity will be investigated elsewhere.
55. Durden, J. A.; Heywood, D. L. J. Org. Chem. 1971, 36, 1306-1307.
56. Japanese Kokai, Tokyo, 1984; Chem. Abstr. 1985, 102, 135675.
57. Burger, K.; Thomas, K. Chem. Ztg. 1988, 112, 109-111; Chem. Abstr. 1989, 110, 23805.
58. Burger, K.; Thomas, K. Chem. Ztg. 1988, 112, 109-111; Chem. Abstr. 1989, 110, 23805.