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(i) Nakamichi, N.; Kawashita, Y.; Hayashi, M. Org. Lett. 2002, 4, 22, 3955-3957.
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0142106411
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A related oxidative synthesis of benzoxazoles: (k) Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713-3715.
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Kawashita, Y.1
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16
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27144559421
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note
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For representative drugs and pharmacologically active compounds, see The Merck Index Online. The structure search with pyrimidine gave 177 hits, including Bleomycin (glycopeptide antibiotics), Buspirone (anxiolytic), Pyrithiobac (herbicide), and Monastrol (Kinesin EG5 inhibitor).
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17
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0000482661
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Vanden Eynde, J. J.; Audiart, N.; Canonne, V.; Michel, S.; Van Haverbeke, Y.; Kappe, C. O. Heterocycles 1997, 45, 1967-1978.
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Vanden Eynde, J.J.1
Audiart, N.2
Canonne, V.3
Michel, S.4
Van Haverbeke, Y.5
Kappe, C.O.6
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18
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0035697361
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(a) Puchala, A.; Belaj, F.; Bergman, J.; Kappe, C. O. J. Heterocycl. Chem. 2001, 38, 1345-1352.
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Puchala, A.1
Belaj, F.2
Bergman, J.3
Kappe, C.O.4
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20
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0031081522
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Watanabe, M.; Koike, H.; Ishiba, T.; Okada, T.; Seo, S.; Hirai, K. Bioorg. Med. Chem. 1997, 5, 437-444.
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Watanabe, M.1
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Ishiba, T.3
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Seo, S.5
Hirai, K.6
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21
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27144446114
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Unpublished results
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Yamamoto, K. Unpublished results.
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Yamamoto, K.1
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23
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27144518411
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Kadis, V.; Strandins, J.; Khanina, E. L.; Duburs, G. Electrochim. Acta 1989, 34, 899-904.
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Electrochim. Acta
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Kadis, V.1
Strandins, J.2
Khanina, E.L.3
Duburs, G.4
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24
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27144554140
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note
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3 oxidation (for substrate 1i) with use of an ARC apparatus (Fauske, Inc) determined it to be thermally unstable within the test conditions. A runaway event occurred with an onset temperature of 40°C, with heat evolution of 157.5 cal/g (adiabatic rise of 205°C) and severe pressure buildup.
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25
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27144444310
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Jpn. Kokai Tokkyo Koho, 1998, 9 pp; JP 10114755 A2 19980506 Heisei
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Metal-catalyzed oxidations in related systems: Kuwabe, T.; Okuyama, S.; Hashimoto, S. Jpn. Kokai Tokkyo Koho, 1998, 9 pp; JP 10114755 A2 19980506 Heisei.
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Kuwabe, T.1
Okuyama, S.2
Hashimoto, S.3
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26
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27144481551
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note
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4, bleach, and molecular oxygen were tested. Only TBHP gave > 10% (by HPLC area) conversion.
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27
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27144457707
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note
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3 in the aqueous phase, which is introduced from the aqueous TBHP solution.
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28
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27144443324
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note
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A total of 20 equiv of oxidant was used and the reaction was carried out over an extended period of time.
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29
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27144550129
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note
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To eliminate trace amounts of Cu salts introduced from the previous step, the substrate was prepared without a Lewis acid catalyst. See the Supporting Information.
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30
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27144474892
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note
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The carbon numbering of dihydropyrimidines and dihydropyrimidinones depends on the substituent pattern. For clarity, the numbering for compound 1a is used for all the substrates in this letter.
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31
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27144549209
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note
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3
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32
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27144448733
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note
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2 catalyst.
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35
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17444428665
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(c) Yu, J.-Q.; Wu, H.-C.; Corey, E. J. Org. Lett. 2005, 7, 1415-1417.
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Yu, J.-Q.1
Wu, H.-C.2
Corey, E.J.3
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39
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27144532367
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note
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23a the detailed mechanistic investigation was not performed in the present study.
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40
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0037185537
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and references sited therein
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(a) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 845-866 and references sited therein.
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Tetrahedron
, pp. 845-866
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Andrus, M.B.1
Lashley, J.C.2
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42
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0000887096
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(c) Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Banfi, S.; Quici, S. J. Am. Chem. Soc. 1995, 117, 226-232.
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Minisci, F.1
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43
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0347419121
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Copper: (a) Maeda, Y.; Nishimura, T.; Uemura, S. Bull. Chem. Soc. Jpn. 2003, 76, 2399-2403.
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Bull. Chem. Soc. Jpn.
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Maeda, Y.1
Nishimura, T.2
Uemura, S.3
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44
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0025328750
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(b) Capdevielle, P.; Lavigne, A.; Sparfel, D.; Baranne-Lafont, J.; Nguyen, K. C.; Maumy, M. Tetrahedron Lett. 1990, 31, 3305-3308.
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47
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0037419001
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(d) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480-1483.
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48
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0036291459
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(e) Murahashi, S.-I.; Takaya, H.; Naota, T. Pure Appl. Chem. 2002, 74, 19-24.
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Pure Appl. Chem.
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Murahashi, S.-I.1
Takaya, H.2
Naota, T.3
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49
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0034008092
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Murahashi, S.-I.; Takaya, H. 2000, 33, 225-233
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(f) Murahashi, S.-I.; Takaya, H. 2000, 33, 225-233.
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50
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0000007094
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Cobalt: (g) Maruyama, K.; Kusukawa, T.; Higuchi, Y.; Nishinaga, A. Chem. Lett. 1991, 1093-1096.
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Chem. Lett.
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Maruyama, K.1
Kusukawa, T.2
Higuchi, Y.3
Nishinaga, A.4
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51
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27144469465
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note
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3 are involved in the rate-limiting step (unpublished results).
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52
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27144498552
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note
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2 did not occur (Table 2, entry 12).
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54
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27144442003
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note
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26 but cannot exclude the possibility. We thank one of the reviewers for drawing our attention to this pathway.
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56
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27144514665
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note
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As part of our exploratory study, a selection of heterocycles were tested for the dehydrogenation, which further suport the mechanism dipicted in Figure 2. See the Supporting Information.
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57
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27144510532
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note
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The structure of peroxide 15d was determined by 2D-NMR (see the Supporting Information).
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58
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27144475740
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note
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Preliminary results on isotope effects suggest that the cleavage of the C-H bond at C-6 is involved in the rate-limiting step.
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59
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27144463935
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note
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1/2 ∼ <30 min).
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60
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27144463934
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note
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2/heptane by GC area. The product was collected by filtration and washed with the filtrate (2.0 l), then heptane (1.0 l), and the wet cake was dried under vacuum (∼27-29 Torr) at 40°C. The product 2i (666.1 g, 2.29 mol, 96% yield) was obtained as a white powder, with requisite spectroscopic properties. This procedure has been performed on a ∼ 400 kg (input) scale without incident.
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61
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17744365015
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(a) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
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Schultz, M.J.1
Hamilton, S.S.2
Jensen, D.R.3
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4544248275
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(b) Steinhoff, B. A.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 11268-11278.
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Steinhoff, B.A.1
Guzei, I.A.2
Stahl, S.S.3
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64
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18744386111
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Recently, a related oxidation was extended to C-C bond formation. Some representative references: (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968-6969.
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J. Am. Chem. Soc.
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Li, Z.1
Li, C.-J.2
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68
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0346850026
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(e) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312-15313.
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Murahashi, S.-I.1
Komiya, N.2
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