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Volumn 53, Issue 31, 2012, Pages 3994-3997

Synthesis of ethyl 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylate via regioselective dipolar cycloaddition

Author keywords

1,3 Dipolar cycloaddition; Fluorine; Heterocycles; Regioselective

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ETHYL 3 PHENYL 4 (TRIFLUOROMETHYL)ISOXAZOLE 5 CARBOXYATE; NITRILE OXIDE; UNCLASSIFIED DRUG;

EID: 84862674550     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.089     Document Type: Article
Times cited : (19)

References (40)
  • 22
    • 84962376558 scopus 로고    scopus 로고
    • The energy gaps between the HOMO of phenyl nitrile oxide and the LUMO of crotonates are 1.5-2.5 eV smaller than the gaps between the HOMO of crotonates and the LUMO of nitrile oxide. The calculated HOMO coefficients for the 1,3-dipole are 42 for ArCNO and 27 for ArCNO. For related regioselectivity models, see
    • The energy gaps between the HOMO of phenyl nitrile oxide and the LUMO of crotonates are 1.5-2.5 eV smaller than the gaps between the HOMO of crotonates and the LUMO of nitrile oxide. The calculated HOMO coefficients for the 1,3-dipole are 42 for ArCNO and 27 for ArCNO. For related regioselectivity models, see: A. Rastelli, R. Gandolfi, and M.S. Amadè J. Org. Chem. 63 1998 7425
    • (1998) J. Org. Chem. , vol.63 , pp. 7425
    • Rastelli, A.1    Gandolfi, R.2    Amadè, M.S.3
  • 23
    • 0034644620 scopus 로고    scopus 로고
    • references cited therein
    • Y. Hu, and K.N. Houk Tetrahedron 56 2000 8239 and references cited therein
    • (2000) Tetrahedron , vol.56 , pp. 8239
    • Hu, Y.1    Houk, K.N.2
  • 25
    • 51849084295 scopus 로고    scopus 로고
    • Please see Supplementary data for details. The observed regioselectivities were independent on the geometry of the dipolarophile olefin. The use of methyl 2-chloromethylcrotonate affords the isoxazole with opposite regioselectivity, highlighting the effect of the trifluoromethyl group
    • Please see Supplementary data for details. The observed regioselectivities were independent on the geometry of the dipolarophile olefin. The use of methyl 2-chloromethylcrotonate affords the isoxazole with opposite regioselectivity, highlighting the effect of the trifluoromethyl group: J. Lasri, S. Mukhopadhyay, and M. Adília Januárip Charmier J. Heterocycl. Chem. 45 2008 1385
    • (2008) J. Heterocycl. Chem. , vol.45 , pp. 1385
    • Lasri, J.1    Mukhopadhyay, S.2    Adília Januárip Charmier, M.3
  • 27
    • 80054772562 scopus 로고    scopus 로고
    • While this manuscript was in preparation, a similar transformation was reported
    • While this manuscript was in preparation, a similar transformation was reported: D.C. Schmitt, L. Lam, and J.S. Johnson Org. Lett. 13 2011 5136
    • (2011) Org. Lett. , vol.13 , pp. 5136
    • Schmitt, D.C.1    Lam, L.2    Johnson, J.S.3
  • 28
    • 33645547538 scopus 로고    scopus 로고
    • Enolates of 1-oxo-3,3,3-trifluoromethyl compounds undergo extremely facile elimination of fluoride: see
    • Enolates of 1-oxo-3,3,3-trifluoromethyl compounds undergo extremely facile elimination of fluoride: see K. Mikami, and Y. Itoh Chemical Record 6 2006 1
    • (2006) Chemical Record , vol.6 , pp. 1
    • Mikami, K.1    Itoh, Y.2
  • 29
    • 0028290175 scopus 로고
    • Alternatively, 13 can be prepared in 28% yield (unoptimized) by treating the α-ketoester 12 with triethyloxonium tetrafluoroborate in the presence of diisopropylethylamine. Please see Supplementary data for details
    • Alternatively, 13 can be prepared in 28% yield (unoptimized) by treating the α-ketoester 12 with triethyloxonium tetrafluoroborate in the presence of diisopropylethylamine. Please see Supplementary data for details K.K. Bach, H.R. El-Seedi, H.M. Jensen, H.B. Nielsen, I. Thomson, and K.B.G. Torssell Tetrahedron 50 1994 7543
    • (1994) Tetrahedron , vol.50 , pp. 7543
    • Bach, K.K.1    El-Seedi, H.R.2    Jensen, H.M.3    Nielsen, H.B.4    Thomson, I.5    Torssell, K.B.G.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.