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For a recent and exhaustive review on the chemistry of quinone imides, see: Nair, V.; Dhanya, R.; Rajesh, C.; Devipriya, S. Synlett 2005, 2407.
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Nair, V.1
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(a) Engler, T. A.; Chai, W.; Lynch, K. O. Tetrahedron Lett. 1995, 36, 7003.
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Engler, T.A.1
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5
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0000047835
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For examples of the synthetic utility of α,β-unsaturated N,N-dimethylhydrazones for the elaboration of nitrogen heterocycles, see: (a) Serckx-Poncin, B.; Hesbain-Frisque, A.-M.; Ghosez, L. Tetrahedron Lett. 1982, 23, 3261.
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(c) For a review: Pautet, F.; Nebois, P.; Bouaziz, Z.; Pillion, H. Heterocycles 2001, 54, 1095.
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Pautet, F.1
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Pillion, H.4
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8
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0032537701
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This strategy has been exploited in the quinone series for the preparation of various heterocycles: (a) Kitahara, Y.; Tamura, F.; Nishimura, M.; Kubo, A. Tetrahedron 1998, 54, 8421.
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18744364167
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(c) Alvarez, F.; Taleb, A.; Gentili, J.; Nebois, P.; Terreux, R.; Domard, M.; Thozet, A.; Merle, D.; Fillion, H.; Walchshofer, N. Eur. J. Org. Chem. 2005, 1903.
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0001061931
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3) to proceed in a 38% yield (20 h reaction time, 23 °C): Echavarren, A. M. J. Org. Chem. 1990, 55, 4255.
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Echavarren, A.M.1
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13
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33748919167
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note
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For an optimized synthesis of compound 5 involving its selective precipitation, see Supporting Information.
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14
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33748934103
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note
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3 generally contains acid traces which behave as a catalyst for the transformation of the keto compound 5 into the phenol 7.
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15
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33748920249
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note
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1H NMR after a 22 h stay at 25 °C.
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16
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33748925984
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note
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2 nitrogen is 2.21 Å (measured on the X-ray crystal structure).
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17
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0000745912
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Blanco, M. M.; Alonso, M. A.; Avendaño, C.; Menéndez, J. C. Tetrahedron 1996, 52, 5933.
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0030272214
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For some examples: (a) anti-HIV pterocarpans: Engler, T. A.; LaTessa, K. O.; Iyengar, R.; Chai, W.: Agrios, K. Bioorg. Med. Chem. 1996, 4, 1755.
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13944269836
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(c) Melatoninergic agents: Sun, L.-Q.; Takaki, K.; Chen, J.; Bertenshaw, S.; Iben, L.; Mahle, C. D.; Ryan, E.; Wu, D.; Gao, Q.; Xu, C. Bioorg. Med. Chem. Lett. 2005, 25, 1345.
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24
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23944503264
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(d) PPARα agonists: Shi, G. Q.; Dropinski, J. F.; Zhang, Y.; Santini, C.; Sahoo, S. P.; Berger, J. P.; MacNaul, K. L.; Zhou, G.; Agrawal, A.; Alvaro, R.; Cai, T.-q.; Hernandez, M.; Wright, S. D.; Moller, D. E.; Heck, J. V.; Meinke, P. T. J. Med. Chem. 2005, 48, 5589.
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Meinke, P.T.16
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26844490394
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(e) κ-opioid agonists: Chu, G.-H.; Gu, M.; Cassel, J. A.; Belanger, S.; Graczyk, T. M.; DeHaven, R. N.; Conway J.; Koblish, M.; Little, P. J.; Dehaven-Hudkins, D. L.; Dolle, R. E. Bioorg. Med. Chem. 2005, 15, 5114.
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Little, P.J.9
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Dolle, R.E.11
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0012630744
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For recent reports on the preparation of dihydrobenzofuranes, see: (a) Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
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Saito, H.1
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(c) Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778.
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33748922493
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note
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The use of a 2-fold excess of 1a led to a more complex reaction mixture: this could be explained by the oxidizing properties of the quinoid compound 1a.
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32
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33748925279
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note
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2 = H) led to a complex mixture with only traces of the corresponding DHBF.
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33
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For a review on the construction of enantioenriched quaternary stereocenters, see: Trost, B. M.; Jiang, C. Synthesis 2006, 369.
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Trost, B.M.1
Jiang, C.2
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