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Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Black Science: Oxford, U.K., 2000; Chapter 25.
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Degoey, D. A.; Flentge, C. A.; Flosi, W. J.; Grampovnik, D. J.; Kempf, D. J.; Klein, L. L.; Yeung, M. C.; Randolph, J. T.; Wang, X. C.; Yu, S. U.S. Pat. Appl. Publ. U.S. 2005148623; Chem. Abstr. 2005, 143, 133693.
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(a) Degoey, D. A.; Flentge, C. A.; Flosi, W. J.; Grampovnik, D. J.; Kempf, D. J.; Klein, L. L.; Yeung, M. C.; Randolph, J. T.; Wang, X. C.; Yu, S. U.S. Pat. Appl. Publ. U.S. 2005148623; Chem. Abstr. 2005, 143, 133693.
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8
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See Supporting Information for full list of authors. (5) (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
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See Supporting Information for full list of authors. (5) (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
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(b) Burstein, C.; Lehmann, C. W.; Glorius, F. Tetrahedron 2005, 61, 6207.
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Burstein, C.1
Lehmann, C.W.2
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12
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0038547070
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For recent advances in the synthesis of 2-azaindolizines via an acetic acid mediated condensation pathway, see: a
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For recent advances in the synthesis of 2-azaindolizines via an acetic acid mediated condensation pathway, see: (a) Wang, J.; Mason, R.; VanDerveer, K.; Feng, D.; Bu, X. R. J. Org. Chem. 2003, 68, 5415.
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Mason, R.2
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Feng, D.4
Bu, X.R.5
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13
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2353 and references cited therein
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(b) Dyers, J. W. L., Jr.; Mason, R., Jr.; Amoyaw, P.; Bu, X. R. J. Org. Chem. 2005, 70, 2353 and references cited therein.
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J. Org. Chem
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Dyers Jr., J.W.L.1
Mason Jr., R.2
Amoyaw, P.3
Bu, X.R.4
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14
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0037119337
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For recent advances in the synthesis of 2-azaindolizines via an oxidative pathway, see: a
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For recent advances in the synthesis of 2-azaindolizines via an oxidative pathway, see: (a) Bluhm, M. E.; Ciesielski, M.; Görls, H.; Döring, M. Angew. Chem., Int. Ed. 2002, 41, 2962.
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Ciesielski, M.2
Görls, H.3
Döring, M.4
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15
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23844553821
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and references cited therein
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(b) Bluhm, M. E.; Folli, C.; Pufky, D.; Kröger, M.; Walter, O.; Döring, M. Organometallics 2005, 24, 4139 and references cited therein.
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Organometallics
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Bluhm, M.E.1
Folli, C.2
Pufky, D.3
Kröger, M.4
Walter, O.5
Döring, M.6
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16
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84876016119
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Starting thioamides are readily prepared by the three-component Willgerodt-Kindler reaction of an aldehyde, amine, and elemental sulfur. See: Brown, E. V. Synthesis 1975, 358
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Starting thioamides are readily prepared by the three-component Willgerodt-Kindler reaction of an aldehyde, amine, and elemental sulfur. See: Brown, E. V. Synthesis 1975, 358.
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17
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3242757492
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For examples of our recent studies on thioamides, see: (a) Murai, T, Niwa, H, Kimura, T, Shibahara, F. Chem. Lett. 2004, 33, 508
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For examples of our recent studies on thioamides, see: (a) Murai, T.; Niwa, H.; Kimura, T.; Shibahara, F. Chem. Lett. 2004, 33, 508.
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18
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(b) Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.
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Murai, T.1
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Ohta, Y.3
Murakami, M.4
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19
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(c) Murai, T.; Sano, H.; Kawai, H.; Aso, H.; Shibahara, F. J. Org. Chem. 2005, 70, 8148.
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Sano, H.2
Kawai, H.3
Aso, H.4
Shibahara, F.5
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33646762865
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(d) Murai, T.; Toshio, R.; Mutoh, Y. Tetrahedron 2006, 62, 6312.
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Murai, T.1
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Mutoh, Y.3
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21
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37049140187
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As only one example of compound 3, 3b, was reported, see: Glover, E. E.; Vaughan, K. D. J. Chem. Soc., Perkin Trans. 1 1973, 21, 2595.
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As only one example of compound 3, 3b, was reported, see: Glover, E. E.; Vaughan, K. D. J. Chem. Soc., Perkin Trans. 1 1973, 21, 2595.
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22
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33846006326
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See Supporting Information
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See Supporting Information.
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23
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33846009911
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6 (in toluene under reflux for 4 h), but instead, insoluble material was precipitated.
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6 (in toluene under reflux for 4 h), but instead, insoluble material was precipitated.
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24
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0035805264
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For related oxidative desulfurization reactions, such as (a) glycosidation via oxidative activation of a thioether, see
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For related oxidative desulfurization reactions, such as (a) glycosidation via oxidative activation of a thioether, see: Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576.
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Nicolaou, K.C.1
Mitchell, H.J.2
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25
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0001750275
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For oxidative desulfurization-fluorination, see
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(b) For oxidative desulfurization-fluorination, see: Kanie, K.; Mizuno, K.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 1973.
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Kanie, K.1
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11844274689
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Also see review: (c) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
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Also see review: (c) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
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33846009201
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The reaction of 2-azaindolizine 2b and SCl2 provides 3b: see ref 11
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2 provides 3b: see ref 11.
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28
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12344337689
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For a recent review of the Suzuki-Miyaura coupling reaction, see:, Int. Ed, and references cited therein
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For a recent review of the Suzuki-Miyaura coupling reaction, see: Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366 and references cited therein.
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Christmann, U.1
Vilar, R.2
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See Supporting Information for full detailed analytical data Table S1
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See Supporting Information for full detailed analytical data (Table S1).
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33845990891
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See Supporting Information Figures S1 and S2
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See Supporting Information (Figures S1 and S2).
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