-
1
-
-
28244477555
-
-
Shaumann, E, Ed, Georg Thieme Verlag: Stuttgart
-
(a) Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Shaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 11, pp 229-288.
-
(2001)
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations
, vol.11
, pp. 229-288
-
-
Wakefield, B.J.1
-
2
-
-
21344437046
-
-
Pinho e Melo, T. M. V. D. Curr. Org. Chem. 2005, 9, 925-958.
-
(b) Pinho e Melo, T. M. V. D. Curr. Org. Chem. 2005, 9, 925-958.
-
-
-
-
3
-
-
24944553428
-
-
(a) Hansen, T. V.; Wu, P.; Fokin, V. V. J. Org. Chem. 2005, 70, 7761-7764.
-
(2005)
J. Org. Chem
, vol.70
, pp. 7761-7764
-
-
Hansen, T.V.1
Wu, P.2
Fokin, V.V.3
-
5
-
-
20444481767
-
-
(c) Moore, J. E.; Davies, M. W.; Goodenough, K. M.; Wybrow, R. A. J.; York, M.; Johnson, C. N.; Harrity, J. P. A. Tetrahedron 2005, 61, 6707-6714.
-
(2005)
Tetrahedron
, vol.61
, pp. 6707-6714
-
-
Moore, J.E.1
Davies, M.W.2
Goodenough, K.M.3
Wybrow, R.A.J.4
York, M.5
Johnson, C.N.6
Harrity, J.P.A.7
-
6
-
-
38849179369
-
-
(d) Willy, B.; Rominger, F.; Müller, T. J. J. Synthesis 2008, 2, 293-303.
-
(2008)
Synthesis
, vol.2
, pp. 293-303
-
-
Willy, B.1
Rominger, F.2
Müller, T.J.J.3
-
7
-
-
84920798068
-
-
(a) Bandiera, T.; Grünanger, P.; Albini, F. M. J. Heterocycl. Chem. 1992, 29, 1423-1428.
-
(1992)
J. Heterocycl. Chem
, vol.29
, pp. 1423-1428
-
-
Bandiera, T.1
Grünanger, P.2
Albini, F.M.3
-
10
-
-
0028019127
-
-
(b) Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828-5832.
-
(1994)
J. Org. Chem
, vol.59
, pp. 5828-5832
-
-
Nitz, T.J.1
Volkots, D.L.2
Aldous, D.J.3
Oglesby, R.C.4
-
14
-
-
0023850319
-
-
(b) Alberola, A.; Antolin, L. F.; Cuadrado, P.; González, A. M.; Laguna, M. A.; Pulido, F. J. Synthesis 1988, 203-207.
-
(1988)
Synthesis
, pp. 203-207
-
-
Alberola, A.1
Antolin, L.F.2
Cuadrado, P.3
González, A.M.4
Laguna, M.A.5
Pulido, F.J.6
-
15
-
-
0021278315
-
-
(c) Sugai, S.; Sato, K.; Kataoka, K.; Iwasaki, Y.; Tomita, K. Chem. Pharm. Bull. 1984, 32, 530-537.
-
(1984)
Chem. Pharm. Bull
, vol.32
, pp. 530-537
-
-
Sugai, S.1
Sato, K.2
Kataoka, K.3
Iwasaki, Y.4
Tomita, K.5
-
16
-
-
34248220387
-
-
For a recent review on aminoisoxazoles, see
-
(d) For a recent review on aminoisoxazoles, see: Kislyi, V. P.; Danilova, E. B.; Semenov, V. V. Adv. Heterocycl. Chem. 2007, 94, 173-214.
-
(2007)
Adv. Heterocycl. Chem
, vol.94
, pp. 173-214
-
-
Kislyi, V.P.1
Danilova, E.B.2
Semenov, V.V.3
-
17
-
-
34548296982
-
-
(a) Kienle, M.; Dubbaka, S. R.; Brade, K.; Knochel, P. Eur. J. Org. Chem. 2007, 2007, 4166-4176.
-
(2007)
Eur. J. Org. Chem
, vol.2007
, pp. 4166-4176
-
-
Kienle, M.1
Dubbaka, S.R.2
Brade, K.3
Knochel, P.4
-
18
-
-
52049105452
-
-
(b) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 6338-6361
-
-
Surry, D.S.1
Buchwald, S.L.2
-
19
-
-
33746494445
-
-
This issue was also noted by others; see ref 6a. For a review of azoles cross-couplings, see: Schnürch, M, Flasik, R, Khan, A. F, Spina, M, Mihovilovic, M. D, Stanetty, P. Eur. J. Org. Chem. 2006, 2006, 3283-3307
-
This issue was also noted by others; see ref 6a. For a review of azoles cross-couplings, see: Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 2006, 3283-3307.
-
-
-
-
20
-
-
0022629568
-
-
(a) Yevich, J. P.; New, J. S.; Smith, D. W.; Lobeck, W. G.; Catt, J. D.; Mnielli, J. L.; Eison, M. S.; Taylor, D. P.; Riblet, L. A.; Temple, D. L., Jr. J. Med. Chem. 1986, 29, 359-369.
-
(1986)
J. Med. Chem
, vol.29
, pp. 359-369
-
-
Yevich, J.P.1
New, J.S.2
Smith, D.W.3
Lobeck, W.G.4
Catt, J.D.5
Mnielli, J.L.6
Eison, M.S.7
Taylor, D.P.8
Riblet, L.A.9
Temple Jr., D.L.10
-
21
-
-
0028945098
-
-
(b) Urban, F. J.; Breitenbach, R.; Murtiashaw, C. W.; Vanderplas, B. C. Tetrahedron: Assymetry 1995, 6, 321-324.
-
(1995)
Tetrahedron: Assymetry
, vol.6
, pp. 321-324
-
-
Urban, F.J.1
Breitenbach, R.2
Murtiashaw, C.W.3
Vanderplas, B.C.4
-
22
-
-
0007311735
-
-
(c) Böshagen, H. Chem. Ber. 1967, 100, 3326-3330.
-
(1967)
Chem. Ber
, vol.100
, pp. 3326-3330
-
-
Böshagen, H.1
-
23
-
-
64349121831
-
-
For an example with an isoxazolo[4, 5-d]pyrimidine, see: Wagner, E.; Becan, L. Pol. J. Chem. 1995, 69, 70-73.
-
(d) For an example with an isoxazolo[4, 5-d]pyrimidine, see: Wagner, E.; Becan, L. Pol. J. Chem. 1995, 69, 70-73.
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-
-
24
-
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0037420808
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For an example of the reaction of a 3-bromoisoxazoline with nucleobases, see
-
(a) For an example of the reaction of a 3-bromoisoxazoline with nucleobases, see: Coutouli-Argyropoulou, E.; Pilanidou, P. Tetrahedron Lett. 2003, 44, 3755-3758.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 3755-3758
-
-
Coutouli-Argyropoulou, E.1
Pilanidou, P.2
-
25
-
-
84973039763
-
-
For an example using a phenylsulfonyl leaving group, see
-
(b) For an example using a phenylsulfonyl leaving group, see: Anderson, W. K.; Raju, N. Synth. Commun. 1989, 19, 2237-2242.
-
(1989)
Synth. Commun
, vol.19
, pp. 2237-2242
-
-
Anderson, W.K.1
Raju, N.2
-
26
-
-
64349097375
-
Rohm and Haas Company; Improved synthesis of haloformimine compounds
-
Dibromoformaldoxime is commercially available but is readily prepared; see: a, Eur. Pat. Appl. 979814, Feb. 16
-
Dibromoformaldoxime is commercially available but is readily prepared; see: (a) Berrier, J. V.; Umarvadia, A. S.; Rohm and Haas Company; Improved synthesis of haloformimine compounds. Eur. Pat. Appl. 979814, Feb. 16, 2000.
-
(2000)
-
-
Berrier, J.V.1
Umarvadia, A.S.2
-
27
-
-
0026715948
-
-
(b) Rohloff, J. C.; Rubinsun, J., III.; Gardner, J. O. Tetrahedron Lett. 1992, 33, 3113-3116.
-
(1992)
Tetrahedron Lett
, vol.33
, pp. 3113-3116
-
-
Rohloff, J.C.1
Rubinsun III, J.2
Gardner, J.O.3
-
28
-
-
0023278502
-
-
(a) Chiarino, D.; Napoletano, M.; Sala, A. J. Heterocycl. Chem. 1987, 24, 43-46.
-
(1987)
J. Heterocycl. Chem
, vol.24
, pp. 43-46
-
-
Chiarino, D.1
Napoletano, M.2
Sala, A.3
-
29
-
-
0000862102
-
-
(b) De Amici, M.; De Micheli, C.; Carrea, G.; Spezia, S. J. Org. Chem. 1989, 54, 2646-2650.
-
(1989)
J. Org. Chem
, vol.54
, pp. 2646-2650
-
-
De Amici, M.1
De Micheli, C.2
Carrea, G.3
Spezia, S.4
-
30
-
-
77957810963
-
-
For a general discussion of nitrile oxide cycloaddition with alkenes, see
-
(a) For a general discussion of nitrile oxide cycloaddition with alkenes, see: Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G W. Adv. Heterocycl. Chem. 1994, 60, 261-327.
-
(1994)
Adv. Heterocycl. Chem
, vol.60
, pp. 261-327
-
-
Easton, C.J.1
Hughes, C.M.M.2
Savage, G.P.3
Simpson, G.W.4
-
31
-
-
0001656317
-
-
For specific examples using dibromoformaldoxime, see
-
(b) For specific examples using dibromoformaldoxime, see: Caldirola, P.; Ciancaglione, M.; De Amici, M.; De Micheli, C. Tetrahedron Lett. 1986, 27, 4647-4650.
-
(1986)
Tetrahedron Lett
, vol.27
, pp. 4647-4650
-
-
Caldirola, P.1
Ciancaglione, M.2
De Amici, M.3
De Micheli, C.4
-
32
-
-
0025327567
-
-
(c) De Amici, M.; De Micheli, C.; Misani, V. Tetrahedron 1990, 46, 1975-1986.
-
(1990)
Tetrahedron
, vol.46
, pp. 1975-1986
-
-
De Amici, M.1
De Micheli, C.2
Misani, V.3
-
34
-
-
84913068738
-
-
(e) Halling, K.; Thomsen, I.; Torssell, K. B. G. Liebigs Ann. Chem. 1989, 10, 985-990.
-
(1989)
Liebigs Ann. Chem
, vol.10
, pp. 985-990
-
-
Halling, K.1
Thomsen, I.2
Torssell, K.B.G.3
-
35
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64349090916
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See Supporting Information for the synthesis of the 3-bromoisoxazoline substrates
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See Supporting Information for the synthesis of the 3-bromoisoxazoline substrates.
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36
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64349100033
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The reaction was performed at 80 °C (DIPEA, EtOH, oil bath) for various substrates and the conversions were determined by HPLC after 18 h.. Reaction rates are in the order 6j > 6f > 6d > 6e - 6c > 6a
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The reaction was performed at 80 °C (DIPEA, EtOH, oil bath) for various substrates and the conversions were determined by HPLC after 18 h.. Reaction rates are in the order 6j > 6f > 6d > 6e - 6c > 6a
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37
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64349107957
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This is consistent with the fact that we did not observe the addition-elimination of the solvent n-butanol on 3-bromoisoxazolines 6d when sodium carbonate was used as a base. The 3-butoxyisoxazoline 10 was obtained upon replacement of Na2CO3 with K3PO4. See Supporting Information
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4. See Supporting Information.
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38
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64349124327
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Manjarrez, N.; Pérez, H. I.; Soria, O.; Luna, H.; Solis, A. Rev. Soc. Quim. Mex. 2000, 44, 188-193.
-
(2000)
Rev. Soc. Quim. Mex
, vol.44
, pp. 188-193
-
-
Manjarrez, N.1
Pérez, H.I.2
Soria, O.3
Luna, H.4
Solis, A.5
-
39
-
-
0008917420
-
-
For the use of NBS, see
-
(a) For the use of NBS, see: Bianchi, G.; Grünanger, P. Tetrahedron 1965, 21, 817-822.
-
(1965)
Tetrahedron
, vol.21
, pp. 817-822
-
-
Bianchi, G.1
Grünanger, P.2
-
40
-
-
64349111764
-
-
For the use of DDQ, see
-
(b) For the use of DDQ, see: Bianchi, G.; De Amici, M. J. Chem. Res., Synop. 1979, 311.
-
(1979)
J. Chem. Res., Synop
, vol.311
-
-
Bianchi, G.1
De Amici, M.2
-
41
-
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34548662698
-
-
For the use of DBH, see
-
(c) For the use of DBH, see: Azarifar, D.; Maleki, B.; Mohammadi, K. Heterocycles 2007, 71, 683-689.
-
(2007)
Heterocycles
, vol.71
, pp. 683-689
-
-
Azarifar, D.1
Maleki, B.2
Mohammadi, K.3
-
42
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0036324487
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For the use of iodine in DMSO to oxidize 3, 5-diarylisoxazolines, see: Deshmukh, A. Y.; Raghuwanshi, P. B.; Doshi, A. G. Asian J. Chem. 2002, 14, 548-550.
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For the use of iodine in DMSO to oxidize 3, 5-diarylisoxazolines, see: Deshmukh, A. Y.; Raghuwanshi, P. B.; Doshi, A. G. Asian J. Chem. 2002, 14, 548-550.
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43
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64349124553
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See Supporting Information for the effect of various inorganic and organic bases on the oxidation of 8d by iodine
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See Supporting Information for the effect of various inorganic and organic bases on the oxidation of 8d by iodine.
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