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Volumn 70, Issue 18, 2005, Pages 7179-7187

Regio- and stereospecific synthesis of novel 3-enynyl-substituted thioflavones/flavones using a copper-free palladium-catalyzed reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; PALLADIUM; SYNTHESIS (CHEMICAL);

EID: 24144439075     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050828+     Document Type: Article
Times cited : (43)

References (77)
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, Chapter 2.4
    • (d) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 3, Chapter 2.4.
    • (1991) Comprehensive Organic Synthesis , vol.3
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  • 48
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    • (c) Very recently, when this work was in progress, an example on the unexpected formation of porphyrinic enyne was reported, see: Chen, Y.-J.; Lee, G.-H.; Peng, S.-M.; Yeh, C.-Y. Tetrahedron Lett. 2005, 46, 1541;
    • (2005) Tetrahedron Lett. , vol.46 , pp. 1541
    • Chen, Y.-J.1    Lee, G.-H.2    Peng, S.-M.3    Yeh, C.-Y.4
  • 49
    • 17044422935 scopus 로고    scopus 로고
    • corrigendum
    • corrigendum: Tetrahedron Lett. 2005, 46, 3265.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 3265
  • 50
    • 0002389108 scopus 로고
    • (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.
    • (1993) J. Chem. Res., Synop. , pp. 432
    • Kundu, N.G.1    Pal, M.2    Chowdhury, C.3
  • 56
    • 33645596869 scopus 로고    scopus 로고
    • note
    • 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).
  • 57
    • 33645606051 scopus 로고    scopus 로고
    • note
    • (f) This product was detected while monitoring the reaction using TLC where it appeared below the desired product IIIa when visualized under UV light.
  • 58
    • 0027160226 scopus 로고
    • (a) 3-Iodothioflavone and 3-iodoflavone were prepared according to a known procedure, see: Zhang, F. J.; Li, Y. L. Synthesis 1993, 565.
    • (1993) Synthesis , pp. 565
    • Zhang, F.J.1    Li, Y.L.2
  • 59
    • 33645593168 scopus 로고    scopus 로고
    • note
    • (b) All the terminal alkynes used are commercially available.
  • 60
    • 4544255270 scopus 로고    scopus 로고
    • (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.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11164
    • Yao, T.1    Zhang, X.2    Larock, R.C.3
  • 64
    • 33645605480 scopus 로고    scopus 로고
    • note
    • 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.
  • 68
    • 33645604762 scopus 로고    scopus 로고
    • note
    • (c) The stability of A may be accounted for by the contribution from the following resonating structures. Diagram presented.
  • 73
    • 0001268841 scopus 로고
    • 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.
    • (1988) Tetrahedron , vol.44 , pp. 481
    • Arcadi, A.1    Bernocchi, E.2    Burini, A.3    Cacchi, S.4    Marinelli, F.5    Pietroni, B.6
  • 74
    • 33645585473 scopus 로고    scopus 로고
    • note
    • 16a in their study.
  • 77
    • 33645597573 scopus 로고    scopus 로고
    • note
    • 50 of 32 and 33 μM respectively on a tested panel of cancer cell lines [e.g. HT29 (colon), H460 (lung), LoVo (colon), etc.].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.