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0347379865
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note
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For reviews, see: Ref. 1a. For recent some references not included in the above review, see: Ref. 5b; and references cited therein.
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24
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0028150852
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and references cited therein
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4a,b were prepared as follows. Compound (4a): Treatment of propargyl 2-(3,4-dimethoxyphenyl)ethylcarbamate with LiN(TMS)2 (0.3 equiv.) in THF at 66 °C afforded 4a in 90% yield. Compound (4b): Treatment of 3-phenylprop-2-ynyl 2-(3,4-dimethoxyphenyl)ethylcarbamate with NaN(TMS)2 (0.3 equiv.) in the presence of 18-crown-6 (0.3 equiv.) in toluene at 60 °C afforded 4b in 97% yield. And also, see: Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, and Z. Yoshida, Bull. Chem. Soc. Jpn., 1994, 67, 2838; and references cited therein.
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0002666472
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For the first example of oxidation of ethylidenetetrahydro-1,3-oxazin-2-one with MCPBA, see: T. G. Back, O. E. Edwards, and G. A. MacAlpine, Tetrahedron Lett., 1977, 2651.
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0035072554
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For some examples of similar cyclization to oxazolo- or thiazoloisoquinolines, see: (a) I. Osante, M. I. Collado, E. Lete, and N. Sotomayor, Eur. J. Org. Chem., 2001, 1267.
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0035797014
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The synthesis of 3a has been reported, see: M. Bois-Choussy, S. Cadet, M. D. Paolis, and J. Zhu, Tetrahedron Lett., 2001, 42, 4503.
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31
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0347379864
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note
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3, followed by a conventional work-up. The residue was chromatographed (silica gel, hexane-AcOEt = 10: 1) to give 2a (9.9 g) in 85% yield.
-
-
-
-
32
-
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0347379863
-
-
note
-
5: C, 67.90; H, 6.78; N; 3.77. Found: C, 67.79; H, 6.78; N, 3.70.
-
-
-
-
33
-
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0032558671
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For an example of low-temperature method in the kinetic resolution, see: T. Sakai, T. Kishimoto, Y. Tanaka, T. Ema, and M. Utaka, Tetrahedron Lett., 1998, 39, 7881.
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M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, and P. J. Reider, J. Org. Chem., 1999, 64, 2564.
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Reider, P.J.7
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36
-
-
0346749466
-
-
note
-
+) 386.1604, found 386.1601.
-
-
-
-
37
-
-
0346118872
-
-
note
-
2O) δ: 31.38, 34.69, 45.49, 56.52, 56.58, 58.52, 113.9, 114.8, 129.4, 132.6, 147.4, 147.8, 171.5.
-
-
-
-
38
-
-
0347379855
-
-
note
-
3, all diagrams and calculations were performed using maXus crystallographic software package, the refinement was performed using SHELX-97.
-
-
-
-
39
-
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0003666167
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Bruker Nonius, The Netherlands, Mac Science, Japan and The University of Glasgow
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a) S. Mackay, C. J. Gilmore, C. Edwards, N. Stewart, and K. Shankland, maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan and The University of Glasgow, 1999.
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Mackay, S.1
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