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Volumn , Issue 7, 2008, Pages 1042-1044

Synthesis of N,O-heterocycles by intramolecular conjugate addition of a hydroxylamine

Author keywords

Hydroxylamine; Michael addition; Oxazine

Indexed keywords

HETEROCYCLIC COMPOUND; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; OXAZINE DERIVATIVE; TETRAHYDRO 1,2 OXAZINE;

ARTICLE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 42949091992 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072650 Document Type: Article

Times cited : (19)

References (16)

1
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- Perlmutter, P.¹

2
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- For some examples of isoxazolidines, see
- For some examples of isoxazolidines, see: Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957.
- (2002) Tetrahedron , vol.58 , pp. 5957
- Bates, R.W.¹ Sa-Ei, K.²

3
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- Bates, R. W.; Sa-Ei, K. Org. Lett. 2002, 4, 4225.
- (2002) Org. Lett , vol.4 , pp. 4225
- Bates, R.W.¹ Sa-Ei, K.²

4
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- (a) Janza, B.; Studer, A. Synthesis 2002, 2117.
- (2002) Synthesis , pp. 2117
- Janza, B.¹ Studer, A.²

5
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- (b) Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 2001, 12, 3053.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3053
- Tiecco, M.¹ Testaferri, L.² Marini, F.³ Sternativo, S.⁴ Santi, C.⁵ Bagnoli, L.⁶ Temperini, A.⁷

6
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- (a) Connon, S. J.; Blechert, S. Angew Chem. Int. Ed. 2003, 42, 1900.
- (2003) Angew Chem. Int. Ed , vol.42 , pp. 1900
- Connon, S.J.¹ Blechert, S.²

7
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- (b) Vernall, A. J.; Abell, A. D. Aldrichimica Acta 2003, 36, 93.
- (2003) Aldrichimica Acta , vol.36 , pp. 93
- Vernall, A.J.¹ Abell, A.D.²

8
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- For applications of this combination of reactions to the synthesis of tetrahydropyrans, see: a
- For applications of this combination of reactions to the synthesis of tetrahydropyrans, see: (a) Bressy, C.; Allais, F.; Cossy, J. Synlett 2006, 3455.
- (2006) Synlett , pp. 3455
- Bressy, C.¹ Allais, F.² Cossy, J.³

9
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- (b) Bates, R. W.; Song, P. Tetrahedron 2007, 63, 4497.
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10
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- Grochowski, E.; Jurczak, J. Synthesis 1976, 682.
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11
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- This is considered to be much lower than typical loadings: Namba, K, Wang, J, Cui, S, Kishi, Y. Org. Lett. 2005, 7, 5421
- This is considered to be much lower than typical loadings: Namba, K.; Wang, J.; Cui, S.; Kishi, Y. Org. Lett. 2005, 7, 5421.

12
- 42949151498
- 3): δ = 7.65 (m, 4 H, Ar), 7.39 (m, 2 H, Ar), 7.26 (m, 3 H, Ar), 6.99 (dt, J = 6.5, 15.5 Hz, 1 H, H3), 5.87 (d, J = 15.5 Hz, 1 H, H2), 5.31 (t, J = 6.5 Hz, 1 H, H6), 3.72 (s, 3 H, OMe), 2.32 (m, 3 H, H4, H5), 2.00 (m, 1 H, H5).
- 3): δ = 7.65 (m, 4 H, Ar), 7.39 (m, 2 H, Ar), 7.26 (m, 3 H, Ar), 6.99 (dt, J = 6.5, 15.5 Hz, 1 H, H3), 5.87 (d, J = 15.5 Hz, 1 H, H2), 5.31 (t, J = 6.5 Hz, 1 H, H6), 3.72 (s, 3 H, OMe), 2.32 (m, 3 H, H4, H5), 2.00 (m, 1 H, H5).

13
- 42949088632
- Typical Procedure: Hydrazine hydrate (78 μL, 1.6 mmol) was added to a solution of phthalimide 7a (195 mg, 0.53 mmol) in CH 2Cl2 (2 mL, The mixture was stirred for 15 min, and then filtered through a pad of celite to remove the copious colourless precipitate. The filtrate was evaporated to give the oxazine 10a as an oil (122 mg, 98, 1H NMR (300 MHz, CDCl3, δ, 7.23 (m, 5 H, Ph, 5.30 (br s, 1 H, NH, 4.55 (dd, J, 11.2 Hz, 1 H, H6, 3.70 (s, 3 H, OMe, 3.44 (m, 1 H, H3, 2.45 (dd, J, 16.8, 4.7 Hz, 1 H, CHHCO2Me, 2.37 (dd, J, 16.8, 8.5 Hz, 1 H, CHHCO2Me, 1.50-2.00 (m, 4 H, H4, H5, Compound 10c was prepared analogously. 1H NMR (300 MHz, CDCl3, δ, 7.80 (m, 2 H, Ar, 7.50 (m, 3 H, Ar, 7.20 (m, 5 H, Ar, 6.40 (br s, 1 H, NH, 4.59 (dd, J, 10.7, 2.3 Hz, 1 H, H6, 3.59 ddt, J, 10.9, 8.8, 2.8 Hz, 1 H, H
- 2Ph), 1.50-1.90 (m, 4 H, H4, H5).

14
- 42949165134
- The corresponding alcohol is prepared by the reaction between styrene oxide and vinyl magnesium bromide in Et2O. We thank Professor David Knight, University of Cardiff, for this procedure
- 2O. We thank Professor David Knight, University of Cardiff, for this procedure.

15
- 0043194171
- For a discussion of cross-metathesis of different classes of alkenes, see
- For a discussion of cross-metathesis of different classes of alkenes, see: Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 11360
- Chatterjee, A.K.¹ Choi, T.L.² Sanders, D.P.³ Grubbs, R.H.⁴

16
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- Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1 1996, 967.
- (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 967
- Banwell, M.G.¹ Bui, C.T.² Pham, H.T.T.³ Simpson, G.W.⁴

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