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1
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0037424821
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For a review on the synthesis and reactivity of cyclic sulfamidates, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616. Six-ring cyclic sulfamidates, where nitrogen is part of an aziridine ring system, undergo nucleophilic cleavage preferentially at the C-N bond to afford substituted seven-ring cyclic sulfamidates:
-
For a review on the synthesis and reactivity of cyclic sulfamidates, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616. Six-ring cyclic sulfamidates, where nitrogen is part of an aziridine ring system, undergo nucleophilic cleavage preferentially at the C-N bond to afford substituted seven-ring cyclic sulfamidates:
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2
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0001458273
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Gallagher, T.5
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10
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21744433017
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For a recent review covering the synthesis and biological importance of 1,4-benzoxazines, see
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For a recent review covering the synthesis and biological importance of 1,4-benzoxazines, see: Ilaš, J.; Anderluh, P. Š.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325-7348.
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Ilaš, J.1
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Kikelj, D.4
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11
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33751218041
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For recent approaches to 1,4-benzoxazines and related heterocyclic scaffolds, see: a
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For recent approaches to 1,4-benzoxazines and related heterocyclic scaffolds, see: (a) Wolfer, J.; Bekele, T.; Abraham, C J.; Dogo-Isonagie, C.; Lectka, T. Angew. Chem., Int. Ed. 2006, 45, 7398-7400.
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Wolfer, J.1
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Lectka, T.5
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(b) Xu, D.; Chiaroni, A.; Fleury, M.-B.; Largeron, M. J. Org. Chem. 2006, 71, 6374-6381.
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Xu, D.1
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33646439837
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(c) Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron 2006, 62, 4635-4642.
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Feng, G.1
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Dai, W.-M.3
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15
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0028356205
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Openings of 1,2-cyclic sulfamidates with 2-methoxyphenolate have previously been reported in 47-82% isolated yield: Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586.
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Openings of 1,2-cyclic sulfamidates with 2-methoxyphenolate have previously been reported in 47-82% isolated yield: Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586.
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16
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0008165462
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For a review on Pd-catalyzed amination. see: (a) Yang, B. H.; Buchwald. S. L. J. Organomet. Chem. 1999, 576, 125-146. For a previous approach to benzoxazines using Ni(0)-mediated intramolecular amination of aryl chlorides, see:
-
For a review on Pd-catalyzed amination. see: (a) Yang, B. H.; Buchwald. S. L. J. Organomet. Chem. 1999, 576, 125-146. For a previous approach to benzoxazines using Ni(0)-mediated intramolecular amination of aryl chlorides, see:
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17
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0141853186
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For an example using Pd(0)-mediated intramolecular amination of an aryl chloride, see
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(b) Omar-Amrani, R.: Thomas, A.; Brenner, E.; Schneider, R.; Fort, Y. Org. Lett. 2003, 5, 2311-2314. For an example using Pd(0)-mediated intramolecular amination of an aryl chloride, see:
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Omar-Amrani, R.1
Thomas, A.2
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Schneider, R.4
Fort, Y.5
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19
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15744365005
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For a previous synthesis of a quinoxalinone via intramolecular Pd-(0)-mediated amination of an aryl iodide, see: Kitagawa. O.; Takahashi,M.; Yoshikawa, M.; Taguchi. T. J. Am. Chem. Soc. 2005, 127, 3676-3677.
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For a previous synthesis of a quinoxalinone via intramolecular Pd-(0)-mediated amination of an aryl iodide, see: Kitagawa. O.; Takahashi,M.; Yoshikawa, M.; Taguchi. T. J. Am. Chem. Soc. 2005, 127, 3676-3677.
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20
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0142227985
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Other ligands screened included BINAP which gave 9a in 76% yield and Verkade's TTPU ligand (Urgaonkar, S.; Xu, J. H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416-8423) which gave 9a in 86% yield.
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Other ligands screened included BINAP which gave 9a in 76% yield and Verkade's TTPU ligand (Urgaonkar, S.; Xu, J. H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416-8423) which gave 9a in 86% yield.
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21
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34548164316
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An example of a successful Pd-catalyzed cyclization to form a related seven-ring system has been reported
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An example of a successful Pd-catalyzed cyclization to form a related seven-ring system has been reported.
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22
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0042330510
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For the preparation of 10d, see
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For the preparation of 10d, see: Novak, Z.; Timar, G.; Kotschy, A. Tetrahedron 2003, 59, 7509-7513.
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Novak, Z.1
Timar, G.2
Kotschy, A.3
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23
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34548156483
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For selected previous synthetic studies on 20, see: a, US patent, 5,053,407
-
For selected previous synthetic studies on 20, see: (a) Hayakawa, I.; Atarashi, S.; Imamura, M.; Yokohama, S.; Higashihashi, N.; Sakano K.; Ohshima, M. US patent, 1986, 5,053,407.
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Sakano, K.6
Ohshima, M.7
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Tewson has previously reported the synthesis of cyclic sulfamidate 15 in 78% yield from 14: Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169.
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Tewson has previously reported the synthesis of cyclic sulfamidate 15 in 78% yield from 14: Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169.
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