Benzoid-quinoid tautomerism of Schiff bases and their structural analogs: LV. Crown-containing N-phenylimines derived from ortho-hydroxycarbaldehydes of the coumarin series

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• 作者：V. I. Minkin (1264) (2264)
  A. D. Dubonosov (1264)
  V. A. Bren鈥?/a> (2264)
  O. G. Nikolaeva (2264)
  A. V. Tsukanov (1264)
  O. N. Burov (1264)
  A. Yu. Fedyanina (2264)
  
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2013
• 出版时间：March 2013
• 年：2013
• 卷：49
• 期：3
• 页码：374-378
• 全文大小：254KB
• 参考文献：1. Dubonosov, A.D., Tsukanov, A.V., Shepelenko, E.N., Revinskii, Yu.V., Bren鈥? V.A., and Minkin, V.I., / Russ. J. Org. Chem., 2009, vol. 45, p. 200. CrossRef
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  3. Minkin, V.I., Gribanova, T.N., Dubonosov, A.D., Bren鈥? V.A., Minyaev, R.M., Shepelenko, E.N., and Tsukanov, A.V., / Ross. Khim. Zh., 2004, vol. 48, p. 30.
  4. Shepelenko, E.N., Tsukanov, A.V., Revinskii, Yu.V., Dubonosov, A.D., Bren鈥? V.A., and Minkin, V.I., / Russ. J. Org. Chem., 2007, vol. 43, p. 559. CrossRef
  5. Dubonosov, A.D., Minkin, V.I., Bren, V.A., Shepelenko, E.N., Tsukanov, A.V., Starikov, A.G., and Borodkin, G.S., / Tetrahedron, 2008, vol. 64, p. 3160. CrossRef
  6. Tsukanov, A.V., Dubonosov, A.D., Shepelenko, E.N., Bren鈥? V.A., and Minkin, V.I., / Vestn. Yuzhn. Nauch. Tsentra Ross. Akad. Nauk, 2008, vol. 4, no. 3, p. 49.
  7. Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., / J. Mol. Struct., 2011, vol. 998, p. 179. CrossRef
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  9. Nikolaeva, O.G., Gaeva, E.B., Shepelenko, E.N., Tsukanov, A.V., Metelitsa, A.V., Luk鈥檡anov, B.S., Dubonosov, A.D., Bren鈥? V.A., and Minkin, V.I., / Russ. J. Org. Chem., 2009, vol. 45, p. 1091. CrossRef
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• 作者单位：V. I. Minkin (1264) (2264)
  A. D. Dubonosov (1264)
  V. A. Bren鈥?/a> (2264)
  O. G. Nikolaeva (2264)
  A. V. Tsukanov (1264)
  O. N. Burov (1264)
  A. Yu. Fedyanina (2264)
  
  1264. Southern Scientific Center, Russian Academy of Sciences, ul. Chekhova 41, Rostov-on-Don, 344006, Russia
  2264. Research Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia
  
• ISSN：1608-3393

文摘

Schiff bases were synthesized from 3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde, 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde, 6,7-dihydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde, 5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde, and 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde and (15N)aniline or aminobenzo-15-crown-5 (2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecin-15-amine), and tautomeric equilibrium between the hydroxy enimino and keto enamino forms of the 4- and 8-iminomethyl derivatives in solution was revealed by 1H NMR and electronic spectroscopy. Addition of alkaline earth cations to their solutions in acetonitrile displaced the tautomeric equilibrium toward the hydroxy enimino structure due to complex formation with the crown ether fragment.