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2
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0036083053
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For a comprehensive review of different synthetic approaches to the PBD skeleton, see: A. Kamal, M.V. Rao, N. Laxman, G. Ramesh, and G.S.K. Reddy Curr. Med. Chem. Anti-Cancer Agents 2 2002 215 254
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See also: W.-P. Hu, J.-J. Wang, F.-L. Lin, Y.-C. Lin, S.-R. Lin, and M.-H.J. Hsu Org. Chem. 66 2001 2881 2883 and the abundant references therein
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9
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3843140700
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K.K. Kothakonda, and D.S. Bose Bioorg. Med. Chem. Lett. 14 2004 4371 4373 For an application of this approach in the synthesis of tetrahydroisoquinolino- fused benzodiazepines, see:
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Kothakonda, K.K.1
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See, for example: R.L. Clark, K.C. Carter, A.B. Mullen, G.D. Coxon, G. Owusu-Dapaah, E. McFarlane, M.D.D. Thi, M.H. Grant, J.N.A. Tettey, and S.P. Mackay Bioorg. Med. Chem. Lett. 17 2007 624 627
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MacKay, S.P.10
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16
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0003410653
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For some excellent books on the chemistry of hypervalent iodine reagents VCH New York, NY
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For some excellent books on the chemistry of hypervalent iodine reagents, see: A. Varvoglis The Organic Chemistry of Polycoordinated Iodine 1992 VCH New York, NY
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Varvoglis, A.1
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M.A. Ciufolini, N.A. Braun, S. Canesi, M. Ousmer, J. Chang, and D. Chai Synthesis 2007 3759 3772
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26
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77955473262
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Note
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N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates.
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28
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Y. Kikugawa, A. Nagashima, T. Sakamoto, E. Miyazama, and M. Shiiya J. Org. Chem. 68 2003 6739 6744
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Mourato, I.5
Branco, P.S.6
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31
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70349437336
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A related strategy based on the use of the PIFA reagent directed to the synthesis of indeno[1,4]diazepinones has been recently published E. Malamidou-Xenikaki, S. Spyroudis, M. Tsanakopoulou, and D. Hadjipavlou-Litina J. Org. Chem. 74 2009 7315 7321
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34
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77955473021
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Note
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Although literature offers a great amount of examples related to the preparation of PBDs, the preparation of simple pyrrolodiazepines is much more limited. See, for example:
-
-
-
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37
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67349119570
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For alternative approaches to the preparation of PBD-3-ones
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For alternative approaches to the preparation of PBD-3-ones, see: J.Y. Lee, I. Im, T.R. Webb, D. McGrath, M.-R. Song, and Y.-C. Kim Bioorg. Chem. 37 2009 90 95
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37849049626
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D.-M. Zhao, C. Ma, Y. Sha, J.-H. Liu, and M.-S. Cheng Acta Cryst. Sect. E E64, 2008 m54-m55
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Liu, J.-H.4
Cheng, M.-S.5
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40
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77955472526
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Note
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In previous non-published results from our group, we found that the presence of free amino, and also hydroxy groups are not compatible with the PIFA-assisted intramolecular heterocyclization of unsaturated amides.
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-
-
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41
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68449100165
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For some recent advances on the Sonogashira reaction
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For some recent advances on the Sonogashira reaction, see: M.M. Heravi, and S. Sadjadi Tetrahedron 65 2009 7761 7775
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Tetrahedron
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Heravi, M.M.1
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53849112664
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S. Mori, T. Yanase, S. Aoyagi, Y. Monguchi, T. Maegawa, and H. Sajiki Chem. - Eur. J. 14 2008 6994 6999
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Maegawa, T.5
Sajiki, H.6
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46
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77955467129
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Note
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The protection of 17 to afford 18 resulted to be a difficult task. Impossible, when benzyloxycarbonyl chloride was employed, and poorly satisfactory when benzyl para-nitrophenyl carbonate (BNC) was tested.
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-
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47
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0028205009
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Several PBD derivatives similar to 21 with a piperazine substituent at C-11 position has also been targeted as pharmacophores: See, for example J.-Y. Mérour, F. Cossais, S. Piroëlle, and D. Mazéas J. Heterocycl. Chem. 31 1994 87 92 The natural product tilivalline presents the same core with a 3-indolyl substituent at C-11
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J. Heterocycl. Chem.
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, pp. 87-92
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Mérour, J.-Y.1
Cossais, F.2
Piroëlle, S.3
Mazéas, D.4
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48
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77955471886
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Note
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An excess of starting material was employed to avoid an undesired N,N′-diprotection process.
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