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(a) For 3,4-diaryl maleic anhydride, see: Pattabiraman, V. R.; Padakanti, P. S.; Veeramaneni, V. R.; Pal, M.; Yeleswarapu, K. R. Synlett 2002, 947.
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(a) Dimerization of terminal alkynes to the corresponding diyne is often a side reaction under the Sonogashira coupling conditions and this oxidative homocoupling (Glaser coupling) predominates in the presence of oxygen or other reagents, see for example: Kundu, N. G.; Pal, M.; Chowdhury, C. J. Chem. Res., Synop. 1993, 432.
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Batsanov, A. S.; Collings, J. C.; Fairlamb, I. J. S.; Holland, J. P.; Howard, J. A. K.; Lin, Z.; Marder, T. B.; Parsons, A. C.; Ward, R. M.; Zhu, J. J. Org. Chem. 2005, 70, 703 and references therein. CuI in the presence of amine base seemed to have a significant role in such oxidative homocoupling of terminal acetylenes.
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33645596869
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note
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6) δ 179.1, 149.6, 136.9 (2C), 135.3, 132.0, 131.8, 130.2, 129.4 (2C), 128.3 (2C), 128.1 (2C), 128.0, 126.8, 126.6, 101.7, 78.7, 71.9, 63.6, 31.5 (2C), 29.1 (2C).
-
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57
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33645606051
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note
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(f) This product was detected while monitoring the reaction using TLC where it appeared below the desired product IIIa when visualized under UV light.
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58
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(a) 3-Iodothioflavone and 3-iodoflavone were prepared according to a known procedure, see: Zhang, F. J.; Li, Y. L. Synthesis 1993, 565.
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-
-
note
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(b) All the terminal alkynes used are commercially available.
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-
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60
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4544255270
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(c) For the synthesis of simple 3-alkynyl flavones from 3-iodoflavone having no substituent at the 2-position under Sonogashira condition, see: Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11164
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Yao, T.1
Zhang, X.2
Larock, R.C.3
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61
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2942668368
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(d) Kálai, T.; Kulcsár, G.; Ösz, E.; Jekö, J.; Sümegi, B.; Hideg, K. ARKIVOC 2004, Part vii, 266.
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(2004)
ARKIVOC
, Issue.PART VII
, pp. 266
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Kálai, T.1
Kulcsár, G.2
Ösz, E.3
Jekö, J.4
Sümegi, B.5
Hideg, K.6
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64
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33645605480
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note
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3) δ 178.8, 162.9, 162.0, 151.9, 141.7, 141.6, 136.9, 136.3, 134.7, 131.7 (2C), 130.1 (2C), 129.8, 129.4, 128.9, 128.7, 128.3 (2C), 127.8, 125.7, 125.6 (2C), 125.3, 121.5, 114.8 (2C), 114.5 (2C), 89.0, 84.7, 69.9, 56.7.
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67
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0035840170
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See also ref 8b
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(b) Wu, M.-J.; Wei, L.-M.; Lin, C.-F.; Leou, S.-P.; Wei, L.-L.; Tetrahedron 2001, 57, 7839. See also ref 8b.
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(2001)
Tetrahedron
, vol.57
, pp. 7839
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-
Wu, M.-J.1
Wei, L.-M.2
Lin, C.-F.3
Leou, S.-P.4
Wei, L.-L.5
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68
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33645604762
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note
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(c) The stability of A may be accounted for by the contribution from the following resonating structures. Diagram presented.
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-
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69
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0027292115
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(d) Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.
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J. Am. Chem. Soc.
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Nuss, J.M.1
Rennels, R.A.2
Levine, B.H.3
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71
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33744870975
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(b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
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J. Org. Chem.
, vol.63
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Larock, R.C.1
Yum, E.K.2
Refvik, M.D.3
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73
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0001268841
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and references therein
-
(d) A similar effect imparted by hydroxyl groups of acetylenic alcohols was observed during palladium-catalyzed hydroarylation of propargylic alcohols, see: Arcadi, A.; Bernocchi, E.; Burini, A.; Cacchi, S.; Marinelli, F.; Pietroni, B. Tetrahedron 1988, 44, 481 and references therein.
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(1988)
Tetrahedron
, vol.44
, pp. 481
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-
Arcadi, A.1
Bernocchi, E.2
Burini, A.3
Cacchi, S.4
Marinelli, F.5
Pietroni, B.6
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74
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33645585473
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note
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16a in their study.
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-
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75
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0025092539
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See for example: (a) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Indian J. Chem. Sect. B 1990, 29, 814.
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(1990)
Indian J. Chem. Sect. B
, vol.29
, pp. 814
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Ghosh, C.K.1
Bandyopadhyay, C.2
Biswas, S.3
Chakravarty, A.K.4
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76
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(b) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11164
-
-
Yao, T.1
Zhang, X.2
Larock, R.C.3
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77
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33645597573
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note
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50 of 32 and 33 μM respectively on a tested panel of cancer cell lines [e.g. HT29 (colon), H460 (lung), LoVo (colon), etc.].
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