메뉴 건너뛰기




Volumn , Issue 5, 2004, Pages 974-980

Fluorinated heterocyclic compounds - The first example of an irreversible ring-degenerate rearrangement on five-membered heterocycles by attack of an external bidentate nucleophile

Author keywords

Heterocycles; Nucleophilic substitution; Rearrangements; Ring ring interconversion

Indexed keywords

HETEROCYCLIC COMPOUND; HYDROXYLAMINE; OXADIAZOLE DERIVATIVE;

EID: 3142564005     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300737     Document Type: Article
Times cited : (55)

References (120)
  • 4
    • 0023237559 scopus 로고
    • [1d] J. T. Welch, Tetrahedron 1987, 43, 3123-3197.
    • (1987) Tetrahedron , vol.43 , pp. 3123-3197
    • Welch, J.T.1
  • 7
    • 0004060828 scopus 로고
    • (Eds.: M. Hudlicky, A. E. Pavlath), ACS Monograph 187, American Chemical Society, Washington, DC
    • [1g] Chemistry of Organic Fluorine Compounds II, A Critical Review (Eds.: M. Hudlicky, A. E. Pavlath), ACS Monograph 187, American Chemical Society, Washington, DC, 1995.
    • (1995) Chemistry of Organic Fluorine Compounds II, A Critical Review
  • 10
    • 0001715258 scopus 로고    scopus 로고
    • (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Roma
    • [1j] G. G. Furin, Targets in Heterocyclic Systems (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Roma, 1998, vol. 2, pp. 355-441.
    • (1998) Targets in Heterocyclic Systems , vol.2 , pp. 355-441
    • Furin, G.G.1
  • 14
    • 0037071139 scopus 로고    scopus 로고
    • [1n] See the papers published in the Symposium-in-print on Fluorous Chemistry, Tetrahedron 2002, 58, 3823-4132.
    • (2002) Tetrahedron , vol.58 , pp. 3823-4132
  • 35
    • 0000397050 scopus 로고
    • (Ed.: P. de Mayo), Academic Press, New York
    • For photoinduced rearrangements of five-membered heterocycles, see: [10a] A. Padwa, in: Rearrangements in Ground and Excited States (Ed.: P. de Mayo), Academic Press, New York, 1980, vol. III, pp. 501-547.
    • (1980) Rearrangements in Ground and Excited States , vol.3 , pp. 501-547
    • Padwa, A.1
  • 36
  • 37
    • 0001640232 scopus 로고    scopus 로고
    • (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Roma
    • [10c] M. D'Auria, in: Targets in Heterocyclic Systems (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Roma, 1999, vol. 2, pp. 233-279.
    • (1999) Targets in Heterocyclic Systems , vol.2 , pp. 233-279
    • D'Auria, M.1
  • 41
    • 1542534549 scopus 로고
    • [12a] C. W. Bird, Tetrahedron 1985, 41, 1409-1414.
    • (1985) Tetrahedron , vol.41 , pp. 1409-1414
    • Bird, C.W.1
  • 42
    • 0026584775 scopus 로고
    • [12b] C. W. Bird, Tetrahedron 1992, 48, 335-340.
    • (1992) Tetrahedron , vol.48 , pp. 335-340
    • Bird, C.W.1
  • 45
  • 46
    • 4544251528 scopus 로고    scopus 로고
    • note
    • Mechanistic studies on azole-to-azole interconversion reactions involving the 1,2,4-oxadiazole ring have been studied extensively by Spinelli's research group. For several papers on this topic, see refs.[8d,8f,11] and the references cited therein.
  • 47
    • 0000728360 scopus 로고
    • and references cited therein
    • For photoinduced rearrangements involving the 1,2,4-oxadiazole heterocycle, see: [15a] N. Vivona, S. Buscemi, Heterocycles 1995, 41, 2095-2116 and references cited therein.
    • (1995) Heterocycles , vol.41 , pp. 2095-2116
    • Vivona, N.1    Buscemi, S.2
  • 55
    • 84944054159 scopus 로고    scopus 로고
    • (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Elsevier Science
    • [16b] J. C. Jochims, in: Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Elsevier Science, 1996, vol. 4, pp. 179-228.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.4 , pp. 179-228
    • Jochims, J.C.1
  • 64
    • 4544252610 scopus 로고    scopus 로고
    • note
    • Examples of RDR involving a three-atom side-chain have been reported in the 1,2,5-oxadiazole,[20] 1,2,4-thiadiazole,[21] and isothiazole[22] series.
  • 86
    • 33845555418 scopus 로고
    • [24i] S. Hoz, J. Org. Chem. 1982, 47, 3545-3547.
    • (1982) J. Org. Chem. , vol.47 , pp. 3545-3547
    • Hoz, S.1
  • 90
    • 4544368825 scopus 로고    scopus 로고
    • Ref.[17], p. 242
    • [24m] Ref.[17], p. 242.
  • 91
    • 0036566870 scopus 로고    scopus 로고
    • -1). A similar behavior was observed in the case of 3-acetylamino-5-perfluoroheptyl-1,2,4-oxadiazole, which spontaneously rearranges (soon after it is formed by acetylation of the 3-amino-5-perfluoroheptyl derivative) into 5-methyl-3-perfluorooctanoylamino-1, 2,4-oxadiazole; the latter compound remains unchanged upon both melting (at 120 °C) and heating under reflux in ethanol: S. Buscemi, A. Pace, V. Frenna, N. Vivona, Heterocycles 2002, 57, 811-823. In addition, DFT calculations indicate in this case that 5-methyl-5-perfluorooctanoylamino-1,2,4-oxadiazole is more stable, probably because of the peculiar electronic effect of the 5-perfluoroalkyl substituent, as we have confirmed by calculating the energies of 5-methyl-3-trifluoroacetylamino-1,2,4-oxadiazole (the cheaper trifluoromethyl substituent, which simulates well the electronic effect of the larger perfluoroheptyl group) and 3-acetylamino-5-trifluoromethyl-1,2,4-oxadiazole.
    • (2002) Heterocycles , vol.57 , pp. 811-823
    • Buscemi, S.1    Pace, A.2    Frenna, V.3    Vivona, N.4
  • 96
    • 0003978280 scopus 로고
    • Cray Research, Inc.
    • [28b] N. Godbout, D. R. Salahub, J. Andzelm, E. Wimmer, Can. J. Chem. 1992, 70, 560-571. UniChem. Dgauss, version 2.3.1, Cray Research, Inc., 1994.
    • (1994) UniChem. Dgauss, Version 2.3.1
  • 97
    • 4544241650 scopus 로고
    • (Eds.: N. B. Chapman, J. Shorter), Plenum Press, London, chapter 2
    • [29a] J. Shorter, in: Advances in Linear Free Energy Relationships (Eds.: N. B. Chapman, J. Shorter), Plenum Press, London, 1972, chapter 2.
    • (1972) Advances in Linear Free Energy Relationships
    • Shorter, J.1
  • 106
    • 0001264861 scopus 로고
    • Georg Thieme Verlag, Stuttgart, (Heteroarenes III/3)
    • U. Kraatz, in: Methods Org. Chem. (Houben-Weyl), Georg Thieme Verlag, Stuttgart, 1994, vol. E8c (Heteroarenes III/3), pp. 409-525.
    • (1994) Methods Org. Chem. (Houben-Weyl) , vol.E8C , pp. 409-525
    • Kraatz, U.1
  • 107
    • 0032482498 scopus 로고    scopus 로고
    • For recent methodologies for synthesizing 1,2,4-oxadiazoles by the amide oxime route, see: [32a] J. R. Young, R. J. De Vita, Tetrahedron Lett. 1998, 39, 3931-3934.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3931-3934
    • Young, J.R.1    De Vita, R.J.2
  • 110
    • 4544266696 scopus 로고
    • For methodologies for synthesizing fluorinated 1,2,4-oxadiazoles, see: [33a] H. C. Brown, C. R. Wetzel, J. Org. Chem. 1965, 30, 3734-3738.
    • (1965) J. Org. Chem. , vol.30 , pp. 3734-3738
    • Brown, H.C.1    Wetzel, C.R.2
  • 115
    • 4544252609 scopus 로고
    • Jpn. Patent 63162680
    • [33f] O. Rohr, F. Zumstein, Jpn. Patent 63162680, 1988; Chem. Abstr. 1989, 110, 75518.
    • (1989) Chem. Abstr. , vol.110 , pp. 75518
    • Rohr, O.1    Zumstein, F.2
  • 118
    • 4544343573 scopus 로고
    • [33h] E. V. Kabakchi, V. V. Il'in, A. V. Ignatenko, V. A. Ponomarenko, Izv. Akad. Nauk. Ser. Khim. 1992, 1863-1870; Chem. Abstr. 1993, 118, 124429.
    • (1993) Chem. Abstr. , vol.118 , pp. 124429
  • 119
    • 0346351170 scopus 로고
    • J. A. Durden, D. L. Heywood, J. Org. Chem. 1971, 36, 1306-1307. For spectroscopic data, see also: B. A. Trofimov, E. Yu. Schmidt, A. M. Vasil'tsov, A. I. Mikhaleva, A. B. Zaitsev, L. V. Morozova, A. G. Gorshkov, J. Henkelmann, J. D. Arndt, Synthesis 2001, 2427-2430.
    • (1971) J. Org. Chem. , vol.36 , pp. 1306-1307
    • Durden, J.A.1    Heywood, D.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.